Controllable synthesis of benzoxazinones and 2-hydroxy-3-indolinones by visible-light-promoted 5-endo-dig N-radical cyclization cascade
In recent years, significant advances have been made on photoredox-catalyzed N-radical addition to C-C unsaturated bond via N-H bond cleavage. However, these N-centered radical additions have so far been mostly limited to the alkenes, and to our knowledge, N-radical 5-endo-dig cyclizations of alkyne...
Saved in:
| Published in | Cell reports physical science Vol. 2; no. 10; p. 100577 |
|---|---|
| Main Authors | , , , , , , , |
| Format | Journal Article |
| Language | English |
| Published |
Elsevier Inc
20.10.2021
|
| Subjects | |
| Online Access | Get full text |
Cover
Loading…
| Abstract | In recent years, significant advances have been made on photoredox-catalyzed N-radical addition to C-C unsaturated bond via N-H bond cleavage. However, these N-centered radical additions have so far been mostly limited to the alkenes, and to our knowledge, N-radical 5-endo-dig cyclizations of alkynes have been less exploited. Herein, we disclose an 5-endo-dig N-radical cascade cyclization of o-ethynylacetamides by photoredox catalysis involving rare radical cleavage of C-C triple bond, allowing the practical and controllable synthesis of a diverse array of valuable benzoxazinones and 2-hydroxy-3-indolinones in moderate to good yields under mild conditions. Furthermore, a mechanistic rationale for this radical cyclization cascade is supported by various control experiments and theoretical calculations.
[Display omitted]
•N-radical 5-endo-dig cyclization-initiated cascade reaction•Photoredox-catalyzed N-radical addition to C-C triple bond•C-C triple bond cleavage•Controllable and practical synthesis of diverse heterocycles
Tan et al. describe a practical radical cascade reaction via photoredox-catalyzed N-centered radical addition to C-C triple bond, which represents the first N-radical 5-endo-dig cyclization cascade, to the best of their knowledge. This method enables the efficient and controllable synthesis of functionalized benzoxazinones and 2-hydroxy-3-indolinones with wide substrate scope under mild reaction conditions. |
|---|---|
| AbstractList | In recent years, significant advances have been made on photoredox-catalyzed N-radical addition to C-C unsaturated bond via N-H bond cleavage. However, these N-centered radical additions have so far been mostly limited to the alkenes, and to our knowledge, N-radical 5-endo-dig cyclizations of alkynes have been less exploited. Herein, we disclose an 5-endo-dig N-radical cascade cyclization of o-ethynylacetamides by photoredox catalysis involving rare radical cleavage of C-C triple bond, allowing the practical and controllable synthesis of a diverse array of valuable benzoxazinones and 2-hydroxy-3-indolinones in moderate to good yields under mild conditions. Furthermore, a mechanistic rationale for this radical cyclization cascade is supported by various control experiments and theoretical calculations.
[Display omitted]
•N-radical 5-endo-dig cyclization-initiated cascade reaction•Photoredox-catalyzed N-radical addition to C-C triple bond•C-C triple bond cleavage•Controllable and practical synthesis of diverse heterocycles
Tan et al. describe a practical radical cascade reaction via photoredox-catalyzed N-centered radical addition to C-C triple bond, which represents the first N-radical 5-endo-dig cyclization cascade, to the best of their knowledge. This method enables the efficient and controllable synthesis of functionalized benzoxazinones and 2-hydroxy-3-indolinones with wide substrate scope under mild reaction conditions. |
| ArticleNumber | 100577 |
| Author | Zhai, Tong-Yi Sun, Qing Zhou, Jin-Mei Tan, Tong-De Liu, Bin-Yang Li, Long Ye, Long-Wu Qian, Peng-Cheng |
| Author_xml | – sequence: 1 givenname: Tong-De surname: Tan fullname: Tan, Tong-De organization: State Key Laboratory of Physical Chemistry of Solid Surfaces, Key Laboratory of Chemical Biology of Fujian Province, and College of Chemistry and Chemical Engineering, Xiamen University, Xiamen 361005, China – sequence: 2 givenname: Tong-Yi surname: Zhai fullname: Zhai, Tong-Yi organization: State Key Laboratory of Physical Chemistry of Solid Surfaces, Key Laboratory of Chemical Biology of Fujian Province, and College of Chemistry and Chemical Engineering, Xiamen University, Xiamen 361005, China – sequence: 3 givenname: Bin-Yang surname: Liu fullname: Liu, Bin-Yang organization: State Key Laboratory of Physical Chemistry of Solid Surfaces, Key Laboratory of Chemical Biology of Fujian Province, and College of Chemistry and Chemical Engineering, Xiamen University, Xiamen 361005, China – sequence: 4 givenname: Long surname: Li fullname: Li, Long organization: Institute of New Materials & Industry Technology, College of Chemistry & Materials Engineering, Wenzhou University, Wenzhou 325035, China – sequence: 5 givenname: Peng-Cheng surname: Qian fullname: Qian, Peng-Cheng email: qpc@wzu.edu.cn organization: Institute of New Materials & Industry Technology, College of Chemistry & Materials Engineering, Wenzhou University, Wenzhou 325035, China – sequence: 6 givenname: Qing surname: Sun fullname: Sun, Qing email: 71043@nchu.edu.cn organization: Key Laboratory of Jiangxi Province for Persistent Pollutants Control and Resources Recycle, Nanchang Hangkong University, Nanchang 330063, China – sequence: 7 givenname: Jin-Mei surname: Zhou fullname: Zhou, Jin-Mei organization: State Key Laboratory of Physical Chemistry of Solid Surfaces, Key Laboratory of Chemical Biology of Fujian Province, and College of Chemistry and Chemical Engineering, Xiamen University, Xiamen 361005, China – sequence: 8 givenname: Long-Wu surname: Ye fullname: Ye, Long-Wu email: longwuye@xmu.edu.cn organization: State Key Laboratory of Physical Chemistry of Solid Surfaces, Key Laboratory of Chemical Biology of Fujian Province, and College of Chemistry and Chemical Engineering, Xiamen University, Xiamen 361005, China |
| BookMark | eNp9kM9OHDEMxiMEEhR4AU55gWyTzH-JS7UqBQm1l_YcZRKH9SokqyRCO_sCvHZnWA6IAydbtn-f7e8bOQ0xACE3gq8EF-337Wpv0m4luRRzgTddd0IuZNu2rOrb-vRDfk6uc95yzmUjRNfzC_K6jqGk6L0ePdA8hbKBjJlGR0cIh7jXB1zWZaqDpZJtJpvifmIVw2Cjf--NE33BjLME8_i0KWyX4nMsYGnDYJ5jFp_ob5a0RaM9NZPxeNAFY6BGZ6MtXJEzp32G6_d4Sf7d_fy7vmePf349rH88MlPVdWHD6PjgQHKQrtO1tKLSfOxqobtqlM3QOS4aZwe5xEHoxnDj-q61ULeysX11SeRR16SYcwKndgmfdZqU4GpxU23V4qZa3FRHN2eo_wQZLG_nl6TRf43eHlGYn3pBSCobhGDAYgJTlI34Ff4fJBKVMw |
| CitedBy_id | crossref_primary_10_1021_acs_orglett_3c00319 crossref_primary_10_1039_D3GC03971D crossref_primary_10_1126_sciadv_adg4648 crossref_primary_10_1039_D3CC01390A crossref_primary_10_1039_D4QO00552J crossref_primary_10_1016_j_checat_2021_10_004 crossref_primary_10_1021_acs_orglett_2c03222 crossref_primary_10_1002_adsc_202300013 crossref_primary_10_1021_acs_orglett_2c01296 crossref_primary_10_3390_molecules29235710 crossref_primary_10_1021_acs_joc_2c02113 |
| Cites_doi | 10.1021/cr100359d 10.1039/C9QO00094A 10.1016/j.ejmech.2011.01.009 10.1039/C5SC02402A 10.1039/D0GC01522A 10.14233/ajchem.2014.16108 10.1039/C9CC05295J 10.1039/C5CS00852B 10.1021/bi00303a026 10.1055/s-1995-4860 10.1021/acs.orglett.5b02118 10.1002/anie.201702953 10.1021/ja801478n 10.1021/acs.accounts.0c00417 10.1016/S0960-894X(97)10010-5 10.1039/C6SC01095D 10.1039/C7CC03262E 10.1021/acs.accounts.0c00090 10.1016/j.ejmech.2007.02.004 10.1021/jo9008904 10.1021/jacs.6b08094 10.1021/jacs.5b03619 10.1039/C7CS00572E 10.1021/acscatal.7b03078 10.1039/C8CC04618B 10.1021/jo401091w 10.1021/jacs.0c06294 10.1021/ja035695t 10.1016/0960-894X(96)00455-6 10.1021/jacs.8b10387 10.1039/b204879e 10.1016/j.scib.2017.01.016 10.1021/ol503150c 10.1039/C9SC06511C 10.1016/S1872-2067(19)63278-X 10.1021/acscatal.7b01385 10.1021/ja4115192 10.1038/ncomms11188 10.1021/acs.accounts.6b00272 10.1021/jm00121a047 10.1002/anie.201904698 10.1039/D0SC01459A 10.1021/ja203191f 10.1021/jacs.5b09671 10.1021/ja050976h 10.14233/ajchem.2013.12846 10.1007/s00044-010-9475-2 10.1002/anie.201406491 10.1016/j.bioorg.2017.01.001 10.1039/b613443m 10.1021/acs.accounts.9b00472 10.1021/jacs.0c01332 10.1021/np060395l 10.1021/ja309580a 10.1021/acs.orglett.7b01609 10.1007/s00044-011-9626-0 10.1016/j.chempr.2018.11.014 10.1039/C8CS00386F 10.1021/acs.chemrev.6b00018 10.1039/C7QO00152E 10.1016/j.ejmech.2010.03.046 10.1021/jm970394d 10.1021/acs.chemrev.0c00030 10.1021/ja00770a006 10.1021/jacs.5b05377 10.1021/jacs.6b13113 10.31635/ccschem.019.20180026 10.1021/acs.orglett.6b02142 10.1021/acscatal.9b00966 10.1039/C5CS00655D 10.1021/ja00022a029 10.1021/cr010182v 10.1039/C7CC09871E 10.1021/np990408d 10.1021/jm00164a002 10.1016/S1995-7645(13)60092-9 10.1021/jacs.9b13975 |
| ContentType | Journal Article |
| Copyright | 2021 The Authors |
| Copyright_xml | – notice: 2021 The Authors |
| DBID | 6I. AAFTH AAYXX CITATION |
| DOI | 10.1016/j.xcrp.2021.100577 |
| DatabaseName | ScienceDirect Open Access Titles Elsevier:ScienceDirect:Open Access CrossRef |
| DatabaseTitle | CrossRef |
| DatabaseTitleList | |
| DeliveryMethod | fulltext_linktorsrc |
| Discipline | Sciences (General) |
| EISSN | 2666-3864 |
| ExternalDocumentID | 10_1016_j_xcrp_2021_100577 S2666386421002927 |
| GroupedDBID | 6I. AAEDW AAFTH AAXUO ACHIH ACLIJ AITUG ALMA_UNASSIGNED_HOLDINGS AMRAJ EBS FDB GROUPED_DOAJ M41 M~E NCXOZ OK1 ROL 0R~ AALRI AAMRU AAYWO AAYXX ACVFH ADCNI ADVLN AEUPX AFPUW AIGII AKBMS AKRWK AKYEP APXCP CITATION |
| ID | FETCH-LOGICAL-c344t-9bf09fe20e2f7a42d13a0b741a73b2597f015fd92f01591a5c0cf876de4625d83 |
| ISSN | 2666-3864 |
| IngestDate | Thu Apr 24 23:05:17 EDT 2025 Tue Jul 01 03:20:28 EDT 2025 Tue Jul 25 21:02:18 EDT 2023 |
| IsDoiOpenAccess | true |
| IsOpenAccess | true |
| IsPeerReviewed | true |
| IsScholarly | true |
| Issue | 10 |
| Keywords | cyclizations tandem reaction radicals photocatalysis heterocycles |
| Language | English |
| License | This is an open access article under the CC BY-NC-ND license. |
| LinkModel | OpenURL |
| MergedId | FETCHMERGED-LOGICAL-c344t-9bf09fe20e2f7a42d13a0b741a73b2597f015fd92f01591a5c0cf876de4625d83 |
| OpenAccessLink | http://dx.doi.org/10.1016/j.xcrp.2021.100577 |
| ParticipantIDs | crossref_primary_10_1016_j_xcrp_2021_100577 crossref_citationtrail_10_1016_j_xcrp_2021_100577 elsevier_sciencedirect_doi_10_1016_j_xcrp_2021_100577 |
| ProviderPackageCode | CITATION AAYXX |
| PublicationCentury | 2000 |
| PublicationDate | 2021-10-20 |
| PublicationDateYYYYMMDD | 2021-10-20 |
| PublicationDate_xml | – month: 10 year: 2021 text: 2021-10-20 day: 20 |
| PublicationDecade | 2020 |
| PublicationTitle | Cell reports physical science |
| PublicationYear | 2021 |
| Publisher | Elsevier Inc |
| Publisher_xml | – name: Elsevier Inc |
| References | Huang, Hao, Li, Tu, Jiang (bib3) 2018; 54 Alabugin, Timokhin, Abrams, Manoharan, Abrams, Ghiviriga (bib6) 2008; 130 Vasilevsky, Baranov, Mamatyuk, Gatilov, Alabugin (bib48) 2009; 74 Shu, Li, Tan, Yuan, Ye (bib42) 2017; 62 Wang, Chen, Zhang, Sun, Zhu, Ye (bib37) 2020; 142 Sivaguru, Wang, Zanoni, Bi (bib44) 2019; 48 Zhao, Xia (bib21) 2018; 47 Zhao, Chen, Yan, Chen, Xiao (bib32) 2017; 19 Fenton, Newton, Wyman, Bagge, Dron, Riddell, Jones (bib58) 1989; 32 Aitken, Bradbury, Burns, Morrison (bib8) 1995 Carletti, Banaigs, Amade (bib62) 2000; 63 Roos, Demaerel, Graff, Knowles (bib26) 2020; 142 Sagadevan, Charpe, Ragupathi, Hwang (bib46) 2017; 139 Khan, Naqvi, Shahzad, Mahmood, Yar, Zahoor (bib51) 2013; 25 Wei, Chen, Hu, Yang, Lu, Xiao (bib30) 2015; 17 Xiao, Li, Fang, Cui, Thiel (bib45) 2018; 140 Gupta, Kashaw, Jain, Rajak, Soni, Stables (bib64) 2011; 20 Tan, Chen, Yang, Wang, Su, Hong, Zhou, Ye (bib41) 2019; 55 Jatav, Mishra, Kashaw, Stables (bib66) 2008; 43 Yang, Bai, Sun, Dai (bib68) 2014; 16 Powers, Asgian, Ekici, James (bib53) 2002; 102 Alabugin, Manoharan (bib5) 2005; 127 Jiang, Studer (bib20) 2019; 1 Wang, Chen, Wang, Xu, Ye (bib38) 2020; 22 Khan, Afzal, Hussain, Naqvi, Bari, Shahzad, Yar, Mahmood, Bukhari, Mansha (bib50) 2014; 26 Kumar, Shrivastava, Pandeya, Stables (bib65) 2011; 46 Gentry, Knowles (bib22) 2016; 49 Hsieh, Yu, Chang, Hwang (bib52) 2010; 45 Yu, Chen, Xiao (bib43) 2021; 121 Tan, Zhu, Bu, Deng, Chen, Liu, Ye (bib40) 2019; 58 Peng, Wei, Han, Chen, Yu, Han (bib74) 2017; 7 Shi, Li, Zhang, Wang (bib12) 2017; 4 Johnson, Bringley, Wilson, Lewis, Beck, Matzger (bib10) 2003; 125 Yu, Zhao, Chen, Xiao, Chen (bib15) 2020; 53 Wu, Hsu, Jao (bib61) 2006; 69 Kärkäs (bib16) 2017; 7 Amrein, Studer (bib9) 2002 Krantz, Spencer, Tam, Liak, Copp, Thomas, Rafferty (bib57) 1990; 33 Zhu, Das, Bui, Zhou, Curran, Rueping (bib78) 2013; 135 Wang, Tan, Wang, Yuan, Zhang, Zhu, Zhu, Zhou, Ye (bib39) 2017; 53 Stephenson, Yoon, MacMillan (bib13) 2018 Young, Martin (bib72) 1972; 94 Xu, Wang, Zhu (bib69) 2013; 135 Brachet, Marzo, Selkti, König, Belmont (bib35) 2016; 7 Sharma, Kumar, Kumarim, Singh, Kaushik (bib63) 2012; 21 Bordwell, Ji (bib73) 1991; 113 Choi, Knowles (bib23) 2015; 137 Xu, Wang, Zhu (bib67) 2015; 137 Chen, Guo, Zhao, Chen, Xiao (bib33) 2018; 54 Skubi, Blum, Yoon (bib14) 2016; 116 Verma, Kumar (bib71) 2016; 18 Zard (bib19) 2008; 37 Alabugin, Gold (bib34) 2013; 78 Zheng, Gutiérrez-Bonet, Molander (bib27) 2019; 5 Xiong, Zhang (bib18) 2016; 45 Ren, Lu (bib2) 2019; 40 Yaremenko, Radulov, Medvedev, Krivoshchapov, Belyakova, Korlyukov, Ilovaisky, Terent Ev, Alabugin (bib75) 2020; 142 Alabugin, Gilmore, Manoharan (bib7) 2011; 133 Pagire, Kreitmeier, Reiser (bib11) 2017; 56 Mohapatra, Datta (bib55) 1997; 7 Jarvest, Parratt, Debouck, Gorniak, Jennings (bib56) 1996; 6 Wille (bib4) 2013; 113 Nguyen, Zhu, Knowles (bib25) 2019; 9 Miller, Choi, Orbe, Knowles (bib24) 2015; 137 Xiong, Xu (bib1) 2019; 52 Hays, Caprathe, Gilmore, Amin, Emmerling, Michael, Nadimpalli, Nath, Raser, Stafford (bib54) 1998; 41 Hedstrom, Moorman, Dobbs, Abeles (bib59) 1984; 23 Gomes, Vil, Terent’ev, Alabugin (bib77) 2015; 6 Hong, Ye (bib36) 2020; 53 Lang, Wang (bib70) 2019; 6 Elliott, Dos Passos Gomes, Evoniuk, Alabugin (bib76) 2020; 11 Chen, Hu, Lu, Xiao (bib17) 2016; 45 Marasini, Rahim, Perveen, Karim, Mohammed Khan, Atta-Ur-Rahman, Choudhary (bib49) 2017; 70 Rao, Rao, Rao (bib60) 2013; 6 Hu, Qi, Chen, Zhao, Wei, Lan, Xiao (bib31) 2016; 7 Zheng, Zhang, Saeednia, Zhou, Anna, Hong, Molander (bib28) 2020; 11 Hu, Chen, Wei, Liu, Deng, Beauchemin, Xiao (bib29) 2014; 53 Shen, Zhang, Liang, Jiao (bib47) 2016; 138 Stephenson (10.1016/j.xcrp.2021.100577_bib13) 2018 Miller (10.1016/j.xcrp.2021.100577_bib24) 2015; 137 Shen (10.1016/j.xcrp.2021.100577_bib47) 2016; 138 Khan (10.1016/j.xcrp.2021.100577_bib50) 2014; 26 Jiang (10.1016/j.xcrp.2021.100577_bib20) 2019; 1 Yang (10.1016/j.xcrp.2021.100577_bib68) 2014; 16 Ren (10.1016/j.xcrp.2021.100577_bib2) 2019; 40 Powers (10.1016/j.xcrp.2021.100577_bib53) 2002; 102 Wille (10.1016/j.xcrp.2021.100577_bib4) 2013; 113 Xiao (10.1016/j.xcrp.2021.100577_bib45) 2018; 140 Pagire (10.1016/j.xcrp.2021.100577_bib11) 2017; 56 Gomes (10.1016/j.xcrp.2021.100577_bib77) 2015; 6 Amrein (10.1016/j.xcrp.2021.100577_bib9) 2002 Brachet (10.1016/j.xcrp.2021.100577_bib35) 2016; 7 Chen (10.1016/j.xcrp.2021.100577_bib17) 2016; 45 Choi (10.1016/j.xcrp.2021.100577_bib23) 2015; 137 Alabugin (10.1016/j.xcrp.2021.100577_bib34) 2013; 78 Wei (10.1016/j.xcrp.2021.100577_bib30) 2015; 17 Xiong (10.1016/j.xcrp.2021.100577_bib18) 2016; 45 Zheng (10.1016/j.xcrp.2021.100577_bib27) 2019; 5 Wang (10.1016/j.xcrp.2021.100577_bib38) 2020; 22 Marasini (10.1016/j.xcrp.2021.100577_bib49) 2017; 70 Alabugin (10.1016/j.xcrp.2021.100577_bib7) 2011; 133 Shi (10.1016/j.xcrp.2021.100577_bib12) 2017; 4 Bordwell (10.1016/j.xcrp.2021.100577_bib73) 1991; 113 Wu (10.1016/j.xcrp.2021.100577_bib61) 2006; 69 Verma (10.1016/j.xcrp.2021.100577_bib71) 2016; 18 Gentry (10.1016/j.xcrp.2021.100577_bib22) 2016; 49 Tan (10.1016/j.xcrp.2021.100577_bib40) 2019; 58 Huang (10.1016/j.xcrp.2021.100577_bib3) 2018; 54 Kärkäs (10.1016/j.xcrp.2021.100577_bib16) 2017; 7 Vasilevsky (10.1016/j.xcrp.2021.100577_bib48) 2009; 74 Nguyen (10.1016/j.xcrp.2021.100577_bib25) 2019; 9 Wang (10.1016/j.xcrp.2021.100577_bib37) 2020; 142 Alabugin (10.1016/j.xcrp.2021.100577_bib5) 2005; 127 Sivaguru (10.1016/j.xcrp.2021.100577_bib44) 2019; 48 Wang (10.1016/j.xcrp.2021.100577_bib39) 2017; 53 Zhu (10.1016/j.xcrp.2021.100577_bib78) 2013; 135 Hu (10.1016/j.xcrp.2021.100577_bib31) 2016; 7 Zhao (10.1016/j.xcrp.2021.100577_bib32) 2017; 19 Sagadevan (10.1016/j.xcrp.2021.100577_bib46) 2017; 139 Krantz (10.1016/j.xcrp.2021.100577_bib57) 1990; 33 Peng (10.1016/j.xcrp.2021.100577_bib74) 2017; 7 Aitken (10.1016/j.xcrp.2021.100577_bib8) 1995 Jarvest (10.1016/j.xcrp.2021.100577_bib56) 1996; 6 Fenton (10.1016/j.xcrp.2021.100577_bib58) 1989; 32 Shu (10.1016/j.xcrp.2021.100577_bib42) 2017; 62 Mohapatra (10.1016/j.xcrp.2021.100577_bib55) 1997; 7 Hedstrom (10.1016/j.xcrp.2021.100577_bib59) 1984; 23 Yaremenko (10.1016/j.xcrp.2021.100577_bib75) 2020; 142 Rao (10.1016/j.xcrp.2021.100577_bib60) 2013; 6 Zheng (10.1016/j.xcrp.2021.100577_bib28) 2020; 11 Yu (10.1016/j.xcrp.2021.100577_bib15) 2020; 53 Alabugin (10.1016/j.xcrp.2021.100577_bib6) 2008; 130 Yu (10.1016/j.xcrp.2021.100577_bib43) 2021; 121 Tan (10.1016/j.xcrp.2021.100577_bib41) 2019; 55 Sharma (10.1016/j.xcrp.2021.100577_bib63) 2012; 21 Hays (10.1016/j.xcrp.2021.100577_bib54) 1998; 41 Chen (10.1016/j.xcrp.2021.100577_bib33) 2018; 54 Hu (10.1016/j.xcrp.2021.100577_bib29) 2014; 53 Zard (10.1016/j.xcrp.2021.100577_bib19) 2008; 37 Khan (10.1016/j.xcrp.2021.100577_bib51) 2013; 25 Xu (10.1016/j.xcrp.2021.100577_bib69) 2013; 135 Johnson (10.1016/j.xcrp.2021.100577_bib10) 2003; 125 Skubi (10.1016/j.xcrp.2021.100577_bib14) 2016; 116 Roos (10.1016/j.xcrp.2021.100577_bib26) 2020; 142 Kumar (10.1016/j.xcrp.2021.100577_bib65) 2011; 46 Zhao (10.1016/j.xcrp.2021.100577_bib21) 2018; 47 Carletti (10.1016/j.xcrp.2021.100577_bib62) 2000; 63 Xu (10.1016/j.xcrp.2021.100577_bib67) 2015; 137 Young (10.1016/j.xcrp.2021.100577_bib72) 1972; 94 Hsieh (10.1016/j.xcrp.2021.100577_bib52) 2010; 45 Lang (10.1016/j.xcrp.2021.100577_bib70) 2019; 6 Elliott (10.1016/j.xcrp.2021.100577_bib76) 2020; 11 Gupta (10.1016/j.xcrp.2021.100577_bib64) 2011; 20 Xiong (10.1016/j.xcrp.2021.100577_bib1) 2019; 52 Jatav (10.1016/j.xcrp.2021.100577_bib66) 2008; 43 Hong (10.1016/j.xcrp.2021.100577_bib36) 2020; 53 |
| References_xml | – volume: 9 start-page: 4502 year: 2019 end-page: 4507 ident: bib25 article-title: PCET-enabled olefin hydroamidation reactions with publication-title: ACS Catal. – volume: 142 start-page: 3636 year: 2020 end-page: 3644 ident: bib37 article-title: Ynamide smiles rearrangement triggered by visible-light-mediated regioselective ketyl-ynamide coupling: rapid access to functionalized indoles and isoquinolines publication-title: J. Am. Chem. Soc. – volume: 113 start-page: 8398 year: 1991 end-page: 8401 ident: bib73 article-title: Effects of structural changes on acidities and homolytic bond dissociation energies of the hydrogen-nitrogen bonds in amidines, carboxamides, and thiocarboxamides publication-title: J. Am. Chem. Soc. – volume: 139 start-page: 2896 year: 2017 end-page: 2899 ident: bib46 article-title: Visible light copper photoredox-catalyzed aerobic oxidative coupling of phenols and terminal alkynes: regioselective synthesis of functionalized ketones via C≡C triple bond cleavage publication-title: J. Am. Chem. Soc. – volume: 53 start-page: 2003 year: 2020 end-page: 2019 ident: bib36 article-title: Transition metal-catalyzed tandem reactions of ynamides for divergent N-heterocycle synthesis publication-title: Acc. Chem. Res. – volume: 46 start-page: 1006 year: 2011 end-page: 1018 ident: bib65 article-title: Design, synthesis and potential 6 Hz psychomotor seizure test activity of some novel 2-(substituted)-3-[substituted]aminoquinazolin-4(3H)-one publication-title: Eur. J. Med. Chem. – volume: 137 start-page: 13492 year: 2015 end-page: 13495 ident: bib24 article-title: Catalytic olefin hydroamidation enabled by proton-coupled electron transfer publication-title: J. Am. Chem. Soc. – volume: 1 start-page: 38 year: 2019 end-page: 49 ident: bib20 article-title: Chemistry with N-centered radicals generated by single-electron transfer-oxidation using photoredox catalysis publication-title: CCS Chem. – volume: 21 start-page: 1136 year: 2012 end-page: 1148 ident: bib63 article-title: QSAR modeling of synthesized 3-(1,3-benzothiazol-2-yl) 2-phenyl quinazolin-4(3 publication-title: Med. Chem. Res. – volume: 33 start-page: 464 year: 1990 end-page: 479 ident: bib57 article-title: Design and synthesis of 4 publication-title: J. Med. Chem. – volume: 55 start-page: 9923 year: 2019 end-page: 9926 ident: bib41 article-title: Stereoselective synthesis of 2,5-disubstituted pyrrolidines via gold-catalysed anti-Markovnikov hydroamination-initiated tandem reactions publication-title: Chem. Commun. (Camb.) – volume: 7 start-page: 7830 year: 2017 end-page: 7834 ident: bib74 article-title: Dioxygen activation via Cu-catalyzed cascade radical reaction: an approach to isoxazoline/cyclic nitrone-featured α-ketols publication-title: ACS Catal. – volume: 69 start-page: 1467 year: 2006 end-page: 1470 ident: bib61 article-title: Indole alkaloids from publication-title: J. Nat. Prod. – volume: 135 start-page: 1823 year: 2013 end-page: 1829 ident: bib78 article-title: Oxygen switch in visible-light photoredox catalysis: radical additions and cyclizations and unexpected C-C-bond cleavage reactions publication-title: J. Am. Chem. Soc. – volume: 16 start-page: 6216 year: 2014 end-page: 6219 ident: bib68 article-title: Biosynthetically inspired divergent approach to monoterpene indole alkaloids: total synthesis of mersicarpine, leuconodines B and D, leuconoxine, melodinine E, leuconolam, and rhazinilam publication-title: Org. Lett. – volume: 6 start-page: 537 year: 2013 end-page: 543 ident: bib60 article-title: Hepatoprotective and antioxidant capacity of publication-title: Asian Pac. J. Trop. Med. – volume: 47 start-page: 2591 year: 2018 end-page: 2608 ident: bib21 article-title: Recent advances in radical-based C-N bond formation via photo-/electrochemistry publication-title: Chem. Soc. Rev. – volume: 45 start-page: 3069 year: 2016 end-page: 3087 ident: bib18 article-title: New amination strategies based on nitrogen-centered radical chemistry publication-title: Chem. Soc. Rev. – volume: 113 start-page: 813 year: 2013 end-page: 853 ident: bib4 article-title: Radical cascades initiated by intermolecular radical addition to alkynes and related triple bond systems publication-title: Chem. Rev. – start-page: 1592 year: 2002 end-page: 1593 ident: bib9 article-title: Intramolecular radical hydrosilylation—the first radical 5- publication-title: Chem. Commun. (Camb.) – volume: 63 start-page: 981 year: 2000 end-page: 983 ident: bib62 article-title: Matemone, a new bioactive bromine-containing oxindole alkaloid from the Indian Ocean sponge publication-title: J. Nat. Prod. – volume: 142 start-page: 14588 year: 2020 end-page: 14607 ident: bib75 article-title: How to build rigid oxygen-rich tricyclic heterocycles from triketones and hydrogen peroxide: control of dynamic covalent chemistry with inverse α-Effect publication-title: J. Am. Chem. Soc. – volume: 41 start-page: 1060 year: 1998 end-page: 1067 ident: bib54 article-title: 2-amino-4 publication-title: J. Med. Chem. – volume: 53 start-page: 6848 year: 2017 end-page: 6851 ident: bib39 article-title: Dual gold/photoredox-catalyzed bis-arylative cyclization of chiral homopropargyl sulfonamides with diazonium salts: rapid access to enantioenriched 2,3-dihydropyrroles publication-title: Chem. Commun. (Camb.) – volume: 5 start-page: 339 year: 2019 end-page: 352 ident: bib27 article-title: Merging photoredox PCET with Nickel-catalyzed cross-coupling: cascade amidoarylation of unactivated olefins publication-title: Chem – volume: 54 start-page: 10791 year: 2018 end-page: 10811 ident: bib3 article-title: Recent advances in radical transformations of internal alkynes publication-title: Chem. Commun. (Camb.) – year: 2018 ident: bib13 article-title: Visible Light Photocatalysis in Organic Chemistry – volume: 23 start-page: 1753 year: 1984 end-page: 1759 ident: bib59 article-title: Suicide inactivation of chymotrypsin by benzoxazinones publication-title: Biochemistry – volume: 102 start-page: 4639 year: 2002 end-page: 4750 ident: bib53 article-title: Irreversible inhibitors of serine, cysteine, and threonine proteases publication-title: Chem. Rev. – volume: 19 start-page: 3620 year: 2017 end-page: 3623 ident: bib32 article-title: Photocatalytic hydrazonyl radical-mediated radical cyclization/allylation cascade: synthesis of dihydropyrazoles and tetrahydropyridazines publication-title: Org. Lett. – volume: 140 start-page: 15099 year: 2018 end-page: 15113 ident: bib45 article-title: Mechanism of the visible-light-mediated copper-catalyzed coupling reaction of phenols and alkynes publication-title: J. Am. Chem. Soc. – volume: 74 start-page: 6143 year: 2009 end-page: 6150 ident: bib48 article-title: An unexpected rearrangement that disassembles alkyne moiety through formal nitrogen atom insertion between two acetylenic carbons and related cascade transformations: new approach to Sampangine derivatives and polycyclic aromatic amides publication-title: J. Org. Chem. – volume: 7 start-page: 2527 year: 1997 end-page: 2530 ident: bib55 article-title: Efficient synthesis of biologically important chiral 2-alkylamino benzoxazinones publication-title: Bioorg. Med. Chem. Lett. – volume: 52 start-page: 3339 year: 2019 end-page: 3350 ident: bib1 article-title: Chemistry with electrochemically generated N-centered radicals publication-title: Acc. Chem. Res. – volume: 142 start-page: 5974 year: 2020 end-page: 5979 ident: bib26 article-title: Enantioselective hydroamination of alkenes with sulfonamides enabled by proton-coupled electron transfer publication-title: J. Am. Chem. Soc. – volume: 130 start-page: 10984 year: 2008 end-page: 10995 ident: bib6 article-title: In search of efficient 5- publication-title: J. Am. Chem. Soc. – volume: 22 start-page: 4483 year: 2020 end-page: 4488 ident: bib38 article-title: One-pot synthesis of 2-hydroxymethylindoles via photoredox-catalyzed ketyl-ynamide coupling/1,3-allylic alcohol transposition publication-title: Green Chem. – volume: 58 start-page: 9632 year: 2019 end-page: 9639 ident: bib40 article-title: Copper-catalyzed cascade cyclization of indolyl homopropargyl amides: stereospecific construction of bridged aza-[ publication-title: Angew. Chem. Int. Ed. Engl. – volume: 4 start-page: 1322 year: 2017 end-page: 1330 ident: bib12 article-title: Visible light-induced tandem oxidative cyclization of 2-alkynylanilines with disulfides (diselenides) to 3-sulfenyl- and 3-selenylindoles under transition metal-free and photocatalyst-free conditions publication-title: Org. Chem. Front. – volume: 7 start-page: 5002 year: 2016 end-page: 5006 ident: bib35 article-title: Visible light amination/Smiles cascade: access to phthalazine derivatives publication-title: Chem. Sci. (Camb.) – volume: 137 start-page: 6712 year: 2015 end-page: 6724 ident: bib67 article-title: Total syntheses of (−)-mersicarpine, (−)-scholarisine G, (+)-melodinine E, (−)-leuconoxine, (−)-leuconolam, (−)-leuconodine A, (+)-leuconodine F, and (−)-leuconodine C: self-induced diastereomeric anisochronism (SIDA) phenomenon for scholarisine G and leuconodines A and C publication-title: J. Am. Chem. Soc. – volume: 43 start-page: 135 year: 2008 end-page: 141 ident: bib66 article-title: Synthesis and CNS depressant activity of some novel 3-[5-substituted 1,3,4-thiadiazole-2-yl]-2-styryl quinazoline-4(3 publication-title: Eur. J. Med. Chem. – volume: 56 start-page: 10928 year: 2017 end-page: 10932 ident: bib11 article-title: Visible-light-promoted generation of publication-title: Angew. Chem. Int. Ed. Engl. – volume: 17 start-page: 4464 year: 2015 end-page: 4467 ident: bib30 article-title: Photocatalytic radical trifluoromethylation/cyclization cascade: synthesis of CF publication-title: Org. Lett. – volume: 133 start-page: 12608 year: 2011 end-page: 12623 ident: bib7 article-title: Rules for anionic and radical ring closure of alkynes publication-title: J. Am. Chem. Soc. – volume: 125 start-page: 14708 year: 2003 end-page: 14709 ident: bib10 article-title: Comparison of “polynaphthalenes” prepared by two mechanistically distinct routes publication-title: J. Am. Chem. Soc. – volume: 11 start-page: 4131 year: 2020 end-page: 4137 ident: bib28 article-title: Diastereoselective olefin amidoacylation via photoredox PCET/nickel-dual catalysis: reaction scope and mechanistic insights publication-title: Chem. Sci. (Camb.) – volume: 54 start-page: 6780 year: 2018 end-page: 6783 ident: bib33 article-title: Visible light-driven photocatalytic generation of sulfonamidyl radicals for alkene hydroamination of unsaturated sulfonamides publication-title: Chem. Commun. (Camb.) – volume: 53 start-page: 1066 year: 2020 end-page: 1083 ident: bib15 article-title: When light meets nitrogen-centered radicals: from reagents to catalysts publication-title: Acc. Chem. Res. – volume: 53 start-page: 12163 year: 2014 end-page: 12167 ident: bib29 article-title: Photocatalytic generation of N-centered hydrazonyl radicals: a strategy for hydroamination of β,γ-unsaturated hydrazones publication-title: Angew. Chem. Int. Ed. Engl. – volume: 7 start-page: 4999 year: 2017 end-page: 5022 ident: bib16 article-title: Photochemical generation of nitrogen-centered amidyl, hydrazonyl, and imidyl radicals: methodology developments and catalytic applications publication-title: ACS Catal. – volume: 18 start-page: 4388 year: 2016 end-page: 4391 ident: bib71 article-title: Selective oxidative decarbonylative cleavage of unstrained C(sp(3))-C(sp(2)) bond: synthesis of substituted benzoxazinones publication-title: Org. Lett. – volume: 20 start-page: 1638 year: 2011 end-page: 1642 ident: bib64 article-title: Design and synthesis of some novel 3-[5-(4-Substituted)phenyl-1,3,4-oxadiazole-2yl]-2-phenylquinazoline-4(3 publication-title: Med. Chem. Res. – volume: 78 start-page: 7777 year: 2013 end-page: 7784 ident: bib34 article-title: “Two functional groups in one package”: using both alkyne π-bonds in cascade transformations publication-title: J. Org. Chem. – volume: 48 start-page: 2615 year: 2019 end-page: 2656 ident: bib44 article-title: Cleavage of carbon-carbon bonds by radical reactions publication-title: Chem. Soc. Rev. – volume: 45 start-page: 2044 year: 2016 end-page: 2056 ident: bib17 article-title: Visible light photoredox-controlled reactions of N-radicals and radical ions publication-title: Chem. Soc. Rev. – volume: 62 start-page: 352 year: 2017 end-page: 357 ident: bib42 article-title: Ring strain strategy for the control of regioselectivity. gold-catalyzed anti-Markovnikov cycloisomerization initiated tandem reactions of alkynes publication-title: Sci. Bull. (Beijing) – volume: 37 start-page: 1603 year: 2008 end-page: 1618 ident: bib19 article-title: Recent progress in the generation and use of nitrogen-centred radicals publication-title: Chem. Soc. Rev. – volume: 11 start-page: 6539 year: 2020 end-page: 6555 ident: bib76 article-title: Testing the limits of radical-anionic CH-amination: a 10-million-fold decrease in basicity opens a new path to hydroxyisoindolines publication-title: Chem. Sci. (Camb.) – volume: 49 start-page: 1546 year: 2016 end-page: 1556 ident: bib22 article-title: Synthetic applications of proton-coupled electron transfer publication-title: Acc. Chem. Res. – volume: 70 start-page: 210 year: 2017 end-page: 221 ident: bib49 article-title: Synthesis, structure-activity relationships studies of benzoxazinone derivatives as publication-title: Bioorg. Chem. – start-page: 53 year: 1995 end-page: 54 ident: bib8 article-title: Tandem radical cyclisation in the flash vacuum pyrolysis of 2-methoxyphenyl and 2-methylthiophenyl substituted phosphorus ylides publication-title: Synlett – volume: 6 start-page: 1367 year: 2019 end-page: 1371 ident: bib70 article-title: A carbene-catalyzed tandem isomerization/cyclisation strategy: an efficient assembly of benzoxazinones publication-title: Org. Chem. Front. – volume: 25 start-page: 152 year: 2013 end-page: 156 ident: bib51 article-title: Synthesis and antimicrobial activity of 2-aryl-4 publication-title: Asian J. Org. Chem. – volume: 40 start-page: 1003 year: 2019 end-page: 1019 ident: bib2 article-title: Visible light promoted difunctionalization reactions of alkynes publication-title: Chin. J. Catal. – volume: 7 start-page: 11188 year: 2016 ident: bib31 article-title: Catalytic N-radical cascade reaction of hydrazones by oxidative deprotonation electron transfer and TEMPO mediation publication-title: Nat. Commun. – volume: 127 start-page: 9534 year: 2005 end-page: 9545 ident: bib5 article-title: 5- publication-title: J. Am. Chem. Soc. – volume: 138 start-page: 13147 year: 2016 end-page: 13150 ident: bib47 article-title: Direct tryptophols synthesis from 2-vinylanilines and alkynes via C≡C triple bond cleavage and dioxygen activation publication-title: J. Am. Chem. Soc. – volume: 135 start-page: 19127 year: 2013 end-page: 19130 ident: bib69 article-title: Enantioselective total syntheses of leuconolam-leuconoxine-mersicarpine group monoterpene indole alkaloids publication-title: J. Am. Chem. Soc. – volume: 121 start-page: 506 year: 2021 end-page: 561 ident: bib43 article-title: Visible light-driven radical-mediated C-C bond cleavage/functionalization in organic synthesis publication-title: Chem. Rev. – volume: 32 start-page: 265 year: 1989 end-page: 272 ident: bib58 article-title: Hypolipidemic 2-[4-(1,1-dimethylethyl)phenyl]-4H-3,1-benzoxazin-4-ones. Structure-activity relationships of a novel series of high-density lipoprotein elevators publication-title: J. Med. Chem. – volume: 6 start-page: 2463 year: 1996 end-page: 2466 ident: bib56 article-title: Inhibition of HSV-1 protease by benzoxazinones publication-title: Bioorg. Med. Chem. Lett. – volume: 6 start-page: 6783 year: 2015 end-page: 6791 ident: bib77 article-title: Stereoelectronic source of the anomalous stability of bis-peroxides publication-title: Chem. Sci. (Camb.) – volume: 137 start-page: 9226 year: 2015 end-page: 9229 ident: bib23 article-title: Catalytic alkene carboaminations enabled by oxidative proton-coupled electron transfer publication-title: J. Am. Chem. Soc. – volume: 45 start-page: 3111 year: 2010 end-page: 3115 ident: bib52 article-title: Synthesis and evaluation of benzoxazinone derivatives on activity of human neutrophil elastase and on hemorrhagic shock-induced lung injury in rats publication-title: Eur. J. Med. Chem. – volume: 116 start-page: 10035 year: 2016 end-page: 10074 ident: bib14 article-title: Dual catalysis strategies in photochemical synthesis publication-title: Chem. Rev. – volume: 94 start-page: 5183 year: 1972 end-page: 5185 ident: bib72 article-title: Mechanism of quenching of singlet oxygen by amines publication-title: J. Am. Chem. Soc. – volume: 26 start-page: 4561 year: 2014 end-page: 4565 ident: bib50 article-title: Synthesis of 2-aryl-4 publication-title: Asian J. Org. Chem. – volume: 113 start-page: 813 year: 2013 ident: 10.1016/j.xcrp.2021.100577_bib4 article-title: Radical cascades initiated by intermolecular radical addition to alkynes and related triple bond systems publication-title: Chem. Rev. doi: 10.1021/cr100359d – volume: 6 start-page: 1367 year: 2019 ident: 10.1016/j.xcrp.2021.100577_bib70 article-title: A carbene-catalyzed tandem isomerization/cyclisation strategy: an efficient assembly of benzoxazinones publication-title: Org. Chem. Front. doi: 10.1039/C9QO00094A – volume: 46 start-page: 1006 year: 2011 ident: 10.1016/j.xcrp.2021.100577_bib65 article-title: Design, synthesis and potential 6 Hz psychomotor seizure test activity of some novel 2-(substituted)-3-[substituted]aminoquinazolin-4(3H)-one publication-title: Eur. J. Med. Chem. doi: 10.1016/j.ejmech.2011.01.009 – volume: 6 start-page: 6783 year: 2015 ident: 10.1016/j.xcrp.2021.100577_bib77 article-title: Stereoelectronic source of the anomalous stability of bis-peroxides publication-title: Chem. Sci. (Camb.) doi: 10.1039/C5SC02402A – volume: 22 start-page: 4483 year: 2020 ident: 10.1016/j.xcrp.2021.100577_bib38 article-title: One-pot synthesis of 2-hydroxymethylindoles via photoredox-catalyzed ketyl-ynamide coupling/1,3-allylic alcohol transposition publication-title: Green Chem. doi: 10.1039/D0GC01522A – volume: 26 start-page: 4561 year: 2014 ident: 10.1016/j.xcrp.2021.100577_bib50 article-title: Synthesis of 2-aryl-4H-3,1-benzoxazin-4-ones: a class of α-chymotrypsin inhibitors publication-title: Asian J. Org. Chem. doi: 10.14233/ajchem.2014.16108 – volume: 55 start-page: 9923 year: 2019 ident: 10.1016/j.xcrp.2021.100577_bib41 article-title: Stereoselective synthesis of 2,5-disubstituted pyrrolidines via gold-catalysed anti-Markovnikov hydroamination-initiated tandem reactions publication-title: Chem. Commun. (Camb.) doi: 10.1039/C9CC05295J – volume: 45 start-page: 3069 year: 2016 ident: 10.1016/j.xcrp.2021.100577_bib18 article-title: New amination strategies based on nitrogen-centered radical chemistry publication-title: Chem. Soc. Rev. doi: 10.1039/C5CS00852B – volume: 23 start-page: 1753 year: 1984 ident: 10.1016/j.xcrp.2021.100577_bib59 article-title: Suicide inactivation of chymotrypsin by benzoxazinones publication-title: Biochemistry doi: 10.1021/bi00303a026 – start-page: 53 year: 1995 ident: 10.1016/j.xcrp.2021.100577_bib8 article-title: Tandem radical cyclisation in the flash vacuum pyrolysis of 2-methoxyphenyl and 2-methylthiophenyl substituted phosphorus ylides publication-title: Synlett doi: 10.1055/s-1995-4860 – volume: 17 start-page: 4464 year: 2015 ident: 10.1016/j.xcrp.2021.100577_bib30 article-title: Photocatalytic radical trifluoromethylation/cyclization cascade: synthesis of CF3-containing pyrazolines and isoxazolines publication-title: Org. Lett. doi: 10.1021/acs.orglett.5b02118 – volume: 56 start-page: 10928 year: 2017 ident: 10.1016/j.xcrp.2021.100577_bib11 article-title: Visible-light-promoted generation of α-ketoradicals from vinyl-bromides and molecular oxygen: synthesis of indenones and dihydroindeno[1,2-c]chromenes publication-title: Angew. Chem. Int. Ed. Engl. doi: 10.1002/anie.201702953 – volume: 130 start-page: 10984 year: 2008 ident: 10.1016/j.xcrp.2021.100577_bib6 article-title: In search of efficient 5-endo-dig cyclization of a carbon-centered radical: 40 years from a prediction to another success for the Baldwin rules publication-title: J. Am. Chem. Soc. doi: 10.1021/ja801478n – volume: 53 start-page: 2003 year: 2020 ident: 10.1016/j.xcrp.2021.100577_bib36 article-title: Transition metal-catalyzed tandem reactions of ynamides for divergent N-heterocycle synthesis publication-title: Acc. Chem. Res. doi: 10.1021/acs.accounts.0c00417 – volume: 7 start-page: 2527 year: 1997 ident: 10.1016/j.xcrp.2021.100577_bib55 article-title: Efficient synthesis of biologically important chiral 2-alkylamino benzoxazinones publication-title: Bioorg. Med. Chem. Lett. doi: 10.1016/S0960-894X(97)10010-5 – volume: 7 start-page: 5002 year: 2016 ident: 10.1016/j.xcrp.2021.100577_bib35 article-title: Visible light amination/Smiles cascade: access to phthalazine derivatives publication-title: Chem. Sci. (Camb.) doi: 10.1039/C6SC01095D – volume: 53 start-page: 6848 year: 2017 ident: 10.1016/j.xcrp.2021.100577_bib39 article-title: Dual gold/photoredox-catalyzed bis-arylative cyclization of chiral homopropargyl sulfonamides with diazonium salts: rapid access to enantioenriched 2,3-dihydropyrroles publication-title: Chem. Commun. (Camb.) doi: 10.1039/C7CC03262E – volume: 53 start-page: 1066 year: 2020 ident: 10.1016/j.xcrp.2021.100577_bib15 article-title: When light meets nitrogen-centered radicals: from reagents to catalysts publication-title: Acc. Chem. Res. doi: 10.1021/acs.accounts.0c00090 – volume: 43 start-page: 135 year: 2008 ident: 10.1016/j.xcrp.2021.100577_bib66 article-title: Synthesis and CNS depressant activity of some novel 3-[5-substituted 1,3,4-thiadiazole-2-yl]-2-styryl quinazoline-4(3H)-ones publication-title: Eur. J. Med. Chem. doi: 10.1016/j.ejmech.2007.02.004 – volume: 74 start-page: 6143 year: 2009 ident: 10.1016/j.xcrp.2021.100577_bib48 article-title: An unexpected rearrangement that disassembles alkyne moiety through formal nitrogen atom insertion between two acetylenic carbons and related cascade transformations: new approach to Sampangine derivatives and polycyclic aromatic amides publication-title: J. Org. Chem. doi: 10.1021/jo9008904 – volume: 138 start-page: 13147 year: 2016 ident: 10.1016/j.xcrp.2021.100577_bib47 article-title: Direct tryptophols synthesis from 2-vinylanilines and alkynes via C≡C triple bond cleavage and dioxygen activation publication-title: J. Am. Chem. Soc. doi: 10.1021/jacs.6b08094 – volume: 137 start-page: 6712 year: 2015 ident: 10.1016/j.xcrp.2021.100577_bib67 publication-title: J. Am. Chem. Soc. doi: 10.1021/jacs.5b03619 – volume: 47 start-page: 2591 year: 2018 ident: 10.1016/j.xcrp.2021.100577_bib21 article-title: Recent advances in radical-based C-N bond formation via photo-/electrochemistry publication-title: Chem. Soc. Rev. doi: 10.1039/C7CS00572E – volume: 7 start-page: 7830 year: 2017 ident: 10.1016/j.xcrp.2021.100577_bib74 article-title: Dioxygen activation via Cu-catalyzed cascade radical reaction: an approach to isoxazoline/cyclic nitrone-featured α-ketols publication-title: ACS Catal. doi: 10.1021/acscatal.7b03078 – volume: 54 start-page: 10791 year: 2018 ident: 10.1016/j.xcrp.2021.100577_bib3 article-title: Recent advances in radical transformations of internal alkynes publication-title: Chem. Commun. (Camb.) doi: 10.1039/C8CC04618B – volume: 78 start-page: 7777 year: 2013 ident: 10.1016/j.xcrp.2021.100577_bib34 article-title: “Two functional groups in one package”: using both alkyne π-bonds in cascade transformations publication-title: J. Org. Chem. doi: 10.1021/jo401091w – volume: 142 start-page: 14588 year: 2020 ident: 10.1016/j.xcrp.2021.100577_bib75 article-title: How to build rigid oxygen-rich tricyclic heterocycles from triketones and hydrogen peroxide: control of dynamic covalent chemistry with inverse α-Effect publication-title: J. Am. Chem. Soc. doi: 10.1021/jacs.0c06294 – volume: 125 start-page: 14708 year: 2003 ident: 10.1016/j.xcrp.2021.100577_bib10 article-title: Comparison of “polynaphthalenes” prepared by two mechanistically distinct routes publication-title: J. Am. Chem. Soc. doi: 10.1021/ja035695t – volume: 6 start-page: 2463 year: 1996 ident: 10.1016/j.xcrp.2021.100577_bib56 article-title: Inhibition of HSV-1 protease by benzoxazinones publication-title: Bioorg. Med. Chem. Lett. doi: 10.1016/0960-894X(96)00455-6 – volume: 140 start-page: 15099 year: 2018 ident: 10.1016/j.xcrp.2021.100577_bib45 article-title: Mechanism of the visible-light-mediated copper-catalyzed coupling reaction of phenols and alkynes publication-title: J. Am. Chem. Soc. doi: 10.1021/jacs.8b10387 – start-page: 1592 issue: 15 year: 2002 ident: 10.1016/j.xcrp.2021.100577_bib9 article-title: Intramolecular radical hydrosilylation—the first radical 5-endo-dig cyclisation publication-title: Chem. Commun. (Camb.) doi: 10.1039/b204879e – volume: 62 start-page: 352 year: 2017 ident: 10.1016/j.xcrp.2021.100577_bib42 article-title: Ring strain strategy for the control of regioselectivity. gold-catalyzed anti-Markovnikov cycloisomerization initiated tandem reactions of alkynes publication-title: Sci. Bull. (Beijing) doi: 10.1016/j.scib.2017.01.016 – volume: 16 start-page: 6216 year: 2014 ident: 10.1016/j.xcrp.2021.100577_bib68 article-title: Biosynthetically inspired divergent approach to monoterpene indole alkaloids: total synthesis of mersicarpine, leuconodines B and D, leuconoxine, melodinine E, leuconolam, and rhazinilam publication-title: Org. Lett. doi: 10.1021/ol503150c – volume: 11 start-page: 6539 year: 2020 ident: 10.1016/j.xcrp.2021.100577_bib76 article-title: Testing the limits of radical-anionic CH-amination: a 10-million-fold decrease in basicity opens a new path to hydroxyisoindolines via a mixed C-N/C-O-forming cascade publication-title: Chem. Sci. (Camb.) doi: 10.1039/C9SC06511C – volume: 40 start-page: 1003 year: 2019 ident: 10.1016/j.xcrp.2021.100577_bib2 article-title: Visible light promoted difunctionalization reactions of alkynes publication-title: Chin. J. Catal. doi: 10.1016/S1872-2067(19)63278-X – volume: 7 start-page: 4999 year: 2017 ident: 10.1016/j.xcrp.2021.100577_bib16 article-title: Photochemical generation of nitrogen-centered amidyl, hydrazonyl, and imidyl radicals: methodology developments and catalytic applications publication-title: ACS Catal. doi: 10.1021/acscatal.7b01385 – volume: 135 start-page: 19127 year: 2013 ident: 10.1016/j.xcrp.2021.100577_bib69 article-title: Enantioselective total syntheses of leuconolam-leuconoxine-mersicarpine group monoterpene indole alkaloids publication-title: J. Am. Chem. Soc. doi: 10.1021/ja4115192 – volume: 7 start-page: 11188 year: 2016 ident: 10.1016/j.xcrp.2021.100577_bib31 article-title: Catalytic N-radical cascade reaction of hydrazones by oxidative deprotonation electron transfer and TEMPO mediation publication-title: Nat. Commun. doi: 10.1038/ncomms11188 – volume: 49 start-page: 1546 year: 2016 ident: 10.1016/j.xcrp.2021.100577_bib22 article-title: Synthetic applications of proton-coupled electron transfer publication-title: Acc. Chem. Res. doi: 10.1021/acs.accounts.6b00272 – volume: 32 start-page: 265 year: 1989 ident: 10.1016/j.xcrp.2021.100577_bib58 article-title: Hypolipidemic 2-[4-(1,1-dimethylethyl)phenyl]-4H-3,1-benzoxazin-4-ones. Structure-activity relationships of a novel series of high-density lipoprotein elevators publication-title: J. Med. Chem. doi: 10.1021/jm00121a047 – volume: 58 start-page: 9632 year: 2019 ident: 10.1016/j.xcrp.2021.100577_bib40 article-title: Copper-catalyzed cascade cyclization of indolyl homopropargyl amides: stereospecific construction of bridged aza-[n.2.1] skeletons publication-title: Angew. Chem. Int. Ed. Engl. doi: 10.1002/anie.201904698 – volume: 11 start-page: 4131 year: 2020 ident: 10.1016/j.xcrp.2021.100577_bib28 article-title: Diastereoselective olefin amidoacylation via photoredox PCET/nickel-dual catalysis: reaction scope and mechanistic insights publication-title: Chem. Sci. (Camb.) doi: 10.1039/D0SC01459A – volume: 133 start-page: 12608 year: 2011 ident: 10.1016/j.xcrp.2021.100577_bib7 article-title: Rules for anionic and radical ring closure of alkynes publication-title: J. Am. Chem. Soc. doi: 10.1021/ja203191f – volume: 137 start-page: 13492 year: 2015 ident: 10.1016/j.xcrp.2021.100577_bib24 article-title: Catalytic olefin hydroamidation enabled by proton-coupled electron transfer publication-title: J. Am. Chem. Soc. doi: 10.1021/jacs.5b09671 – volume: 127 start-page: 9534 year: 2005 ident: 10.1016/j.xcrp.2021.100577_bib5 article-title: 5-endo-dig radical cyclizations: “the poor cousins” of the radical cyclizations family publication-title: J. Am. Chem. Soc. doi: 10.1021/ja050976h – volume: 25 start-page: 152 year: 2013 ident: 10.1016/j.xcrp.2021.100577_bib51 article-title: Synthesis and antimicrobial activity of 2-aryl-4H-3,1-benzoxazin-4-ones publication-title: Asian J. Org. Chem. doi: 10.14233/ajchem.2013.12846 – volume: 20 start-page: 1638 year: 2011 ident: 10.1016/j.xcrp.2021.100577_bib64 article-title: Design and synthesis of some novel 3-[5-(4-Substituted)phenyl-1,3,4-oxadiazole-2yl]-2-phenylquinazoline-4(3H)-ones as possible anticonvulsant agent publication-title: Med. Chem. Res. doi: 10.1007/s00044-010-9475-2 – volume: 53 start-page: 12163 year: 2014 ident: 10.1016/j.xcrp.2021.100577_bib29 article-title: Photocatalytic generation of N-centered hydrazonyl radicals: a strategy for hydroamination of β,γ-unsaturated hydrazones publication-title: Angew. Chem. Int. Ed. Engl. doi: 10.1002/anie.201406491 – volume: 70 start-page: 210 year: 2017 ident: 10.1016/j.xcrp.2021.100577_bib49 article-title: Synthesis, structure-activity relationships studies of benzoxazinone derivatives as α-chymotrypsin inhibitors publication-title: Bioorg. Chem. doi: 10.1016/j.bioorg.2017.01.001 – volume: 37 start-page: 1603 year: 2008 ident: 10.1016/j.xcrp.2021.100577_bib19 article-title: Recent progress in the generation and use of nitrogen-centred radicals publication-title: Chem. Soc. Rev. doi: 10.1039/b613443m – volume: 52 start-page: 3339 year: 2019 ident: 10.1016/j.xcrp.2021.100577_bib1 article-title: Chemistry with electrochemically generated N-centered radicals publication-title: Acc. Chem. Res. doi: 10.1021/acs.accounts.9b00472 – volume: 142 start-page: 5974 year: 2020 ident: 10.1016/j.xcrp.2021.100577_bib26 article-title: Enantioselective hydroamination of alkenes with sulfonamides enabled by proton-coupled electron transfer publication-title: J. Am. Chem. Soc. doi: 10.1021/jacs.0c01332 – volume: 69 start-page: 1467 year: 2006 ident: 10.1016/j.xcrp.2021.100577_bib61 article-title: Indole alkaloids from Cephalanceropsis gracilis publication-title: J. Nat. Prod. doi: 10.1021/np060395l – volume: 135 start-page: 1823 year: 2013 ident: 10.1016/j.xcrp.2021.100577_bib78 article-title: Oxygen switch in visible-light photoredox catalysis: radical additions and cyclizations and unexpected C-C-bond cleavage reactions publication-title: J. Am. Chem. Soc. doi: 10.1021/ja309580a – volume: 19 start-page: 3620 year: 2017 ident: 10.1016/j.xcrp.2021.100577_bib32 article-title: Photocatalytic hydrazonyl radical-mediated radical cyclization/allylation cascade: synthesis of dihydropyrazoles and tetrahydropyridazines publication-title: Org. Lett. doi: 10.1021/acs.orglett.7b01609 – volume: 21 start-page: 1136 year: 2012 ident: 10.1016/j.xcrp.2021.100577_bib63 article-title: QSAR modeling of synthesized 3-(1,3-benzothiazol-2-yl) 2-phenyl quinazolin-4(3H)-ones as potent antibacterial agents publication-title: Med. Chem. Res. doi: 10.1007/s00044-011-9626-0 – volume: 5 start-page: 339 year: 2019 ident: 10.1016/j.xcrp.2021.100577_bib27 article-title: Merging photoredox PCET with Nickel-catalyzed cross-coupling: cascade amidoarylation of unactivated olefins publication-title: Chem doi: 10.1016/j.chempr.2018.11.014 – volume: 48 start-page: 2615 year: 2019 ident: 10.1016/j.xcrp.2021.100577_bib44 article-title: Cleavage of carbon-carbon bonds by radical reactions publication-title: Chem. Soc. Rev. doi: 10.1039/C8CS00386F – volume: 116 start-page: 10035 year: 2016 ident: 10.1016/j.xcrp.2021.100577_bib14 article-title: Dual catalysis strategies in photochemical synthesis publication-title: Chem. Rev. doi: 10.1021/acs.chemrev.6b00018 – volume: 4 start-page: 1322 year: 2017 ident: 10.1016/j.xcrp.2021.100577_bib12 article-title: Visible light-induced tandem oxidative cyclization of 2-alkynylanilines with disulfides (diselenides) to 3-sulfenyl- and 3-selenylindoles under transition metal-free and photocatalyst-free conditions publication-title: Org. Chem. Front. doi: 10.1039/C7QO00152E – volume: 45 start-page: 3111 year: 2010 ident: 10.1016/j.xcrp.2021.100577_bib52 article-title: Synthesis and evaluation of benzoxazinone derivatives on activity of human neutrophil elastase and on hemorrhagic shock-induced lung injury in rats publication-title: Eur. J. Med. Chem. doi: 10.1016/j.ejmech.2010.03.046 – volume: 41 start-page: 1060 year: 1998 ident: 10.1016/j.xcrp.2021.100577_bib54 article-title: 2-amino-4H-3,1-benzoxazin-4-ones as inhibitors of C1r serine protease publication-title: J. Med. Chem. doi: 10.1021/jm970394d – volume: 121 start-page: 506 year: 2021 ident: 10.1016/j.xcrp.2021.100577_bib43 article-title: Visible light-driven radical-mediated C-C bond cleavage/functionalization in organic synthesis publication-title: Chem. Rev. doi: 10.1021/acs.chemrev.0c00030 – volume: 94 start-page: 5183 year: 1972 ident: 10.1016/j.xcrp.2021.100577_bib72 article-title: Mechanism of quenching of singlet oxygen by amines publication-title: J. Am. Chem. Soc. doi: 10.1021/ja00770a006 – volume: 137 start-page: 9226 year: 2015 ident: 10.1016/j.xcrp.2021.100577_bib23 article-title: Catalytic alkene carboaminations enabled by oxidative proton-coupled electron transfer publication-title: J. Am. Chem. Soc. doi: 10.1021/jacs.5b05377 – volume: 139 start-page: 2896 year: 2017 ident: 10.1016/j.xcrp.2021.100577_bib46 article-title: Visible light copper photoredox-catalyzed aerobic oxidative coupling of phenols and terminal alkynes: regioselective synthesis of functionalized ketones via C≡C triple bond cleavage publication-title: J. Am. Chem. Soc. doi: 10.1021/jacs.6b13113 – volume: 1 start-page: 38 year: 2019 ident: 10.1016/j.xcrp.2021.100577_bib20 article-title: Chemistry with N-centered radicals generated by single-electron transfer-oxidation using photoredox catalysis publication-title: CCS Chem. doi: 10.31635/ccschem.019.20180026 – volume: 18 start-page: 4388 year: 2016 ident: 10.1016/j.xcrp.2021.100577_bib71 article-title: Selective oxidative decarbonylative cleavage of unstrained C(sp(3))-C(sp(2)) bond: synthesis of substituted benzoxazinones publication-title: Org. Lett. doi: 10.1021/acs.orglett.6b02142 – volume: 9 start-page: 4502 year: 2019 ident: 10.1016/j.xcrp.2021.100577_bib25 article-title: PCET-enabled olefin hydroamidation reactions with N-alkyl amides publication-title: ACS Catal. doi: 10.1021/acscatal.9b00966 – volume: 45 start-page: 2044 year: 2016 ident: 10.1016/j.xcrp.2021.100577_bib17 article-title: Visible light photoredox-controlled reactions of N-radicals and radical ions publication-title: Chem. Soc. Rev. doi: 10.1039/C5CS00655D – volume: 113 start-page: 8398 year: 1991 ident: 10.1016/j.xcrp.2021.100577_bib73 article-title: Effects of structural changes on acidities and homolytic bond dissociation energies of the hydrogen-nitrogen bonds in amidines, carboxamides, and thiocarboxamides publication-title: J. Am. Chem. Soc. doi: 10.1021/ja00022a029 – volume: 102 start-page: 4639 year: 2002 ident: 10.1016/j.xcrp.2021.100577_bib53 article-title: Irreversible inhibitors of serine, cysteine, and threonine proteases publication-title: Chem. Rev. doi: 10.1021/cr010182v – year: 2018 ident: 10.1016/j.xcrp.2021.100577_bib13 – volume: 54 start-page: 6780 year: 2018 ident: 10.1016/j.xcrp.2021.100577_bib33 article-title: Visible light-driven photocatalytic generation of sulfonamidyl radicals for alkene hydroamination of unsaturated sulfonamides publication-title: Chem. Commun. (Camb.) doi: 10.1039/C7CC09871E – volume: 63 start-page: 981 year: 2000 ident: 10.1016/j.xcrp.2021.100577_bib62 article-title: Matemone, a new bioactive bromine-containing oxindole alkaloid from the Indian Ocean sponge Iotrochota purpurea publication-title: J. Nat. Prod. doi: 10.1021/np990408d – volume: 33 start-page: 464 year: 1990 ident: 10.1016/j.xcrp.2021.100577_bib57 article-title: Design and synthesis of 4H-3,1-benzoxazin-4-ones as potent alternate substrate inhibitors of human leukocyte elastase publication-title: J. Med. Chem. doi: 10.1021/jm00164a002 – volume: 6 start-page: 537 year: 2013 ident: 10.1016/j.xcrp.2021.100577_bib60 article-title: Hepatoprotective and antioxidant capacity of Melochia corchorifolia extracts publication-title: Asian Pac. J. Trop. Med. doi: 10.1016/S1995-7645(13)60092-9 – volume: 142 start-page: 3636 year: 2020 ident: 10.1016/j.xcrp.2021.100577_bib37 article-title: Ynamide smiles rearrangement triggered by visible-light-mediated regioselective ketyl-ynamide coupling: rapid access to functionalized indoles and isoquinolines publication-title: J. Am. Chem. Soc. doi: 10.1021/jacs.9b13975 |
| SSID | ssj0002511780 |
| Score | 2.257924 |
| Snippet | In recent years, significant advances have been made on photoredox-catalyzed N-radical addition to C-C unsaturated bond via N-H bond cleavage. However, these... |
| SourceID | crossref elsevier |
| SourceType | Enrichment Source Index Database Publisher |
| StartPage | 100577 |
| SubjectTerms | cyclizations heterocycles photocatalysis radicals tandem reaction |
| Title | Controllable synthesis of benzoxazinones and 2-hydroxy-3-indolinones by visible-light-promoted 5-endo-dig N-radical cyclization cascade |
| URI | https://dx.doi.org/10.1016/j.xcrp.2021.100577 |
| Volume | 2 |
| hasFullText | 1 |
| inHoldings | 1 |
| isFullTextHit | |
| isPrint | |
| link | http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwnV3NT9swFLc6dtllGvvQYAP5sMOmylXixE1znAoITYLLQIJdotixWVGVVrSVKIddufIn7z3b-eiUoY1LWr0mcdT3i_17z--DkE9DA6SDDw0rUm6whZliElZdZhSXskiUTmzW-8np8Pg8_nYhLnq9h1bU0mopB-quM6_kKVoFGegVs2T_Q7P1TUEA30G_cAQNw_GfdDx2ceZTm_60WJdA5nx9EanLu9ktlo7GWvx2h4Czn-sCg1ZYxMAQx2Y99jfgn5hgDrdgU1tVZG4j9ICICqbhPFZMrvqn7CZ3OzpqraY-d7Ov8gWG17cJ7hh9gdVGxLwCgV9nGzeB64k8K6_YQS394VtjW_HlpA4VmqwsCCclu8z9OmvF1qUw8xLvuOA2co4HjTetyqjZCPgEvjBk0chVNh_oDpmftXkbnEHnYuD8EteDW2Urk_IQQ0KE7xqzWWT7O46BQ3AsSZvy5Bl5zsHwwJnz5FfjtUODLLHt-OqH8plYLmjwz6G62U6LwZy9Ii-96UG_Ohxtk54uX5NtP7kv6GdfgfzLG3LfBhatgUVnhm4CiwKw6F-AReWadgOLNsCiNbBoC1jUA-stOT86PBsfM9-xg6kojpcslSZIjeaB5ibJY16EUR5IIK15EkkwtBMD7NPgtACfaZgLFSgD63GhY7DDi1H0jmzhI74nNBKpTopcBoKbOM31KDQiMLpAA14LpXZIWP2zmfLl7LGryjSr4havM9RGhtrInDZ2SL--Zu6KuTx6tqgUlvnXxNHMDAD2yHW7T7zuA3nRvCYfydbyZqX3gPEu5b71FO1bKP4GL9CxgQ |
| linkProvider | ISSN International Centre |
| openUrl | ctx_ver=Z39.88-2004&ctx_enc=info%3Aofi%2Fenc%3AUTF-8&rfr_id=info%3Asid%2Fsummon.serialssolutions.com&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.atitle=Controllable+synthesis+of+benzoxazinones+and+2-hydroxy-3-indolinones+by+visible-light-promoted+5-endo-dig+N-radical+cyclization+cascade&rft.jtitle=Cell+reports+physical+science&rft.au=Tan%2C+Tong-De&rft.au=Zhai%2C+Tong-Yi&rft.au=Liu%2C+Bin-Yang&rft.au=Li%2C+Long&rft.date=2021-10-20&rft.pub=Elsevier+Inc&rft.issn=2666-3864&rft.eissn=2666-3864&rft.volume=2&rft.issue=10&rft_id=info:doi/10.1016%2Fj.xcrp.2021.100577&rft.externalDocID=S2666386421002927 |
| thumbnail_l | http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/lc.gif&issn=2666-3864&client=summon |
| thumbnail_m | http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/mc.gif&issn=2666-3864&client=summon |
| thumbnail_s | http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/sc.gif&issn=2666-3864&client=summon |