A Mild Synthesis of 2‑Substituted Benzothiazoles via Nickel-Catalyzed Intramolecular Oxidative C–H Functionalization
A highly efficient synthetic method for the preparation of 2-aminobenzothiazoles starting from arylthioureas has been reported. By using a nickel catalyst, arylthioureas undergo intramolecular oxidative C–H bond functionalization, giving the desired 2-aminobenzothiazoles in good to excellent yields....
Saved in:
| Published in | Journal of organic chemistry Vol. 85; no. 2; pp. 493 - 500 |
|---|---|
| Main Authors | , , , , , |
| Format | Journal Article |
| Language | English |
| Published |
WASHINGTON
American Chemical Society
17.01.2020
Amer Chemical Soc |
| Subjects | |
| Online Access | Get full text |
Cover
Loading…
| Abstract | A highly efficient synthetic method for the preparation of 2-aminobenzothiazoles starting from arylthioureas has been reported. By using a nickel catalyst, arylthioureas undergo intramolecular oxidative C–H bond functionalization, giving the desired 2-aminobenzothiazoles in good to excellent yields. This protocol features an inexpensive catalyst, low catalyst loading, mild reaction conditions, a short reaction time, and good to excellent yields, and it can be scaled up easily to a gram scale with almost no yields decreasing. |
|---|---|
| AbstractList | A highly efficient synthetic method for the preparation of 2-aminobenzothiazoles starting from arylthioureas has been reported. By using a nickel catalyst, arylthioureas undergo intramolecular oxidative C–H bond functionalization, giving the desired 2-aminobenzothiazoles in good to excellent yields. This protocol features an inexpensive catalyst, low catalyst loading, mild reaction conditions, a short reaction time, and good to excellent yields, and it can be scaled up easily to a gram scale with almost no yields decreasing. A highly efficient synthetic method for the preparation of 2-aminobenzothiazoles starting from arylthioureas has been reported. By using a nickel catalyst, arylthioureas undergo intramolecular oxidative C-H bond functionalization, giving the desired 2-aminobenzothiazoles in good to excellent yields. This protocol features an inexpensive catalyst, low catalyst loading, mild reaction conditions, a short reaction time, and good to excellent yields, and it can be scaled up easily to a gram scale with almost no yields decreasing.A highly efficient synthetic method for the preparation of 2-aminobenzothiazoles starting from arylthioureas has been reported. By using a nickel catalyst, arylthioureas undergo intramolecular oxidative C-H bond functionalization, giving the desired 2-aminobenzothiazoles in good to excellent yields. This protocol features an inexpensive catalyst, low catalyst loading, mild reaction conditions, a short reaction time, and good to excellent yields, and it can be scaled up easily to a gram scale with almost no yields decreasing. |
| Author | Li, Yue-Sheng Gao, Ming-Yuan Dong, Zhi-Bing Chen, Li-Jun Li, Jing-Hang Zhang, Shi-Bo |
| AuthorAffiliation | School of Chemistry and Environmental Engineering Hubei Key Laboratory of Radiation Chemistry and Functional Materials, School of Nuclear Technology and Chemistry & Biology |
| AuthorAffiliation_xml | – name: Hubei Key Laboratory of Radiation Chemistry and Functional Materials, School of Nuclear Technology and Chemistry & Biology – name: School of Chemistry and Environmental Engineering |
| Author_xml | – sequence: 1 givenname: Ming-Yuan surname: Gao fullname: Gao, Ming-Yuan organization: School of Chemistry and Environmental Engineering – sequence: 2 givenname: Jing-Hang surname: Li fullname: Li, Jing-Hang organization: School of Chemistry and Environmental Engineering – sequence: 3 givenname: Shi-Bo surname: Zhang fullname: Zhang, Shi-Bo organization: School of Chemistry and Environmental Engineering – sequence: 4 givenname: Li-Jun surname: Chen fullname: Chen, Li-Jun organization: School of Chemistry and Environmental Engineering – sequence: 5 givenname: Yue-Sheng surname: Li fullname: Li, Yue-Sheng email: frank78929@163.com organization: Hubei Key Laboratory of Radiation Chemistry and Functional Materials, School of Nuclear Technology and Chemistry & Biology – sequence: 6 givenname: Zhi-Bing orcidid: 0000-0002-3354-8318 surname: Dong fullname: Dong, Zhi-Bing email: dzb04982@wit.edu.cn organization: School of Chemistry and Environmental Engineering |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/31845809$$D View this record in MEDLINE/PubMed |
| BookMark | eNqNkkFPFDEUxxuDkQU9ezM9mphZ3rSdTueIExESlAN6btpuJxRnW5x2gN0TX8HwDfkkdN3BgwnRXtrk__u_5r3330M7PniL0NsS5iWQ8kCZOL8MZt5oIBWjL9CsrAgUvAG2g2YAhBSUcLqL9mK8hHyqqnqFdmkpWCWgmaHbQ_zF9Qt8vvLpwkYXcegwebj7dT7qmFwak13gj9avQ7pwah16G_G1U_irMz9sX7QqqX61zsyJT4NaZt2MvRrw2a1bqOSuLW4f7u6P8dHoTXLBq96t1ebxGr3sVB_tm-neR9-PPn1rj4vTs88n7eFpoSjnqWCqploxTTlAV9lGNEQozTprOFcNgBENVVSD6YA3tqtqTXRJKS0VN4LRmu6j99u6V0P4OdqY5NJFY_teeRvGKAkDYHUeFPwbpaRuKCH1puq7CR310i7k1eCWaljJp8Fm4MMWuLE6dNE46439g20WAYJxkTuAUmRa_D_duvR7gm0YfcrWams1Q4hxsJ00k5734XpZgtwkReakyJwUOSUl-w7-8j1997xjamkrjENeZnyWfgSO_9C6 |
| CitedBy_id | crossref_primary_10_1002_ajoc_202200038 crossref_primary_10_1016_j_apcata_2024_119806 crossref_primary_10_1016_j_mcat_2022_112115 crossref_primary_10_1055_s_0041_1737760 crossref_primary_10_1002_asia_202400455 crossref_primary_10_1002_ejoc_202200954 crossref_primary_10_1002_ejoc_202300817 crossref_primary_10_1021_acs_joc_2c01924 crossref_primary_10_1039_D2OB01477G crossref_primary_10_1016_j_cclet_2021_08_070 crossref_primary_10_1007_s10562_024_04835_3 crossref_primary_10_1021_acs_joc_2c01301 crossref_primary_10_1002_ejoc_202200707 crossref_primary_10_1080_17415993_2021_1989436 crossref_primary_10_1021_acs_joc_2c01789 crossref_primary_10_1039_D3RA07209F crossref_primary_10_1021_acs_joc_3c01575 crossref_primary_10_1002_jhet_4627 crossref_primary_10_1002_open_202400185 crossref_primary_10_1016_j_matpr_2021_06_312 crossref_primary_10_1021_acs_joc_1c02747 crossref_primary_10_1002_ejoc_202201196 crossref_primary_10_1021_acs_joc_2c00728 crossref_primary_10_3390_catal13040658 crossref_primary_10_2174_1389557522666220523110521 crossref_primary_10_1021_acsomega_3c09164 crossref_primary_10_1002_ejoc_202101165 crossref_primary_10_1002_celc_202200787 crossref_primary_10_1021_acs_chemrev_4c00303 crossref_primary_10_1016_j_scp_2021_100521 crossref_primary_10_1021_acs_orglett_1c00235 crossref_primary_10_1016_j_rechem_2022_100512 crossref_primary_10_1080_17415993_2022_2141573 crossref_primary_10_1021_acs_joc_1c02353 crossref_primary_10_1021_acs_joc_3c02113 crossref_primary_10_1055_a_1780_1691 crossref_primary_10_1002_slct_202104081 crossref_primary_10_3390_molecules26082190 |
| Cites_doi | 10.1039/B311591G 10.1021/acs.joc.8b02011 10.1039/C7GC02311A 10.1039/C6CC04394A 10.1002/chem.201705016 10.1021/ol900958z 10.3184/174751917X14931424175476 10.1080/00397911.2017.1324033 10.1021/jp511578v 10.1016/j.ejmech.2012.05.028 10.1016/j.bmcl.2005.05.077 10.1080/17415993.2017.1337771 10.1021/jo8010232 10.1021/ol7026366 10.1021/ja017863s 10.1016/j.ejmech.2015.02.023 10.1021/ja408864c 10.1021/acs.joc.7b01683 10.1055/s-0036-1588835 10.1002/anie.200601872 10.1021/ja301493d 10.1002/ejoc.201701081 10.1021/ic9005136 10.1021/jo8002216 10.1055/s-0036-1590200 10.1002/ejoc.201801271 10.1021/acs.joc.8b01644 10.1038/367630a0 10.1039/C1CC16184A 10.1021/ol071248x 10.1039/B907809F 10.1016/j.tet.2008.01.004 10.1055/s-0034-1380141 10.1021/acs.orglett.5b03185 10.1002/hc.21267 10.1021/cr500431s 10.1021/acs.orglett.6b03385 10.1002/anie.200906678 10.1002/adsc.201701506 10.1021/acs.joc.8b02136 10.1016/j.bmc.2014.09.028 10.1002/jhet.5570260425 10.1021/acs.orglett.5b00079 10.1039/c2sc20248d 10.1039/c0cs00182a 10.1021/acs.orglett.7b02911 10.1039/C0GC00418A 10.1002/ejoc.201801122 10.1021/ol802033p 10.1039/c2gc35799b 10.1002/anie.201303838 10.1016/j.cclet.2014.05.015 10.1039/c1cc16184a 10.1039/b311591g 10.1039/c7gc02311a 10.1039/c0gc00418a 10.1039/c6cc04394a 10.1039/b907809f |
| ContentType | Journal Article |
| DBID | AAYXX CITATION 17B 1KM 1KN AOWDO BLEPL DTL EGQ NPM 7X8 7S9 L.6 |
| DOI | 10.1021/acs.joc.9b02543 |
| DatabaseName | CrossRef Web of Knowledge Index Chemicus Current Chemical Reactions Web of Science - Science Citation Index Expanded - 2020 Web of Science Core Collection Science Citation Index Expanded Web of Science Primary (SCIE, SSCI & AHCI) PubMed MEDLINE - Academic AGRICOLA AGRICOLA - Academic |
| DatabaseTitle | CrossRef Web of Science PubMed MEDLINE - Academic AGRICOLA AGRICOLA - Academic |
| DatabaseTitleList | AGRICOLA MEDLINE - Academic Web of Science PubMed |
| Database_xml | – sequence: 1 dbid: NPM name: PubMed url: https://proxy.k.utb.cz/login?url=http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?db=PubMed sourceTypes: Index Database – sequence: 2 dbid: 1KN name: Current Chemical Reactions url: https://proxy.k.utb.cz/login?url=https://www.webofscience.com/wos/woscc/search-with-editions?editions=WOS.CCR sourceTypes: Enrichment Source Index Database |
| DeliveryMethod | fulltext_linktorsrc |
| Discipline | Chemistry |
| EISSN | 1520-6904 |
| EndPage | 500 |
| ExternalDocumentID | 31845809 000508468900018 10_1021_acs_joc_9b02543 d8667403 |
| Genre | Journal Article |
| GrantInformation_xml | – fundername: Hubei Provincial Science and Technology grantid: 2019CFB596 – fundername: Hubei Key Laboratory of Radiation Chemistry and Functional Materials, Hubei University of Science Technology grantid: 2019-20KZ01 – fundername: Ministry-of-Education Key Laboratory for the Synthesis and Application of Organic Functional Molecules, Hubei University grantid: KLSAOFM1810 |
| GroupedDBID | - .K2 29L 55A 5RE 5VS 7~N 85S AABXI ABFLS ABMVS ABPPZ ABPTK ABUCX ABUFD ACGFS ACJ ACNCT ACS AEESW AENEX AFEFF ALMA_UNASSIGNED_HOLDINGS AQSVZ BAANH CJ0 CS3 D0L DU5 DZ EBS ED ED~ F20 F5P GNL IH9 IHE JG JG~ K2 LG6 P2P PZZ ROL RXW TAE TN5 UI2 UKR UPT VF5 VG9 VQA W1F WH7 X XFK YZZ --- -DZ -~X 4.4 53G AAHBH AAYXX ABBLG ABJNI ABLBI ABQRX ACBEA ACGFO ADHLV AGXLV AHGAQ CITATION CUPRZ GGK IH2 TAF XSW YQT ZCA 17B 1KM 1KN BLEPL DTL GROUPED_WOS_WEB_OF_SCIENCE NPM YIN 7X8 7S9 L.6 |
| ID | FETCH-LOGICAL-a366t-4a73ba4b3600f5e98928ab4fec66a900c893a3b0cf069ef57b2b13331a6c84373 |
| IEDL.DBID | ACS |
| ISICitedReferencesCount | 42 |
| ISICitedReferencesURI | https://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcApp=Summon&SrcAuth=ProQuest&DestApp=WOS&DestLinkType=CitingArticles&UT=000508468900018 |
| ISSN | 0022-3263 1520-6904 |
| IngestDate | Fri Jul 11 09:28:43 EDT 2025 Fri Jul 11 05:44:53 EDT 2025 Wed Feb 19 02:31:11 EST 2025 Wed Jul 09 20:47:32 EDT 2025 Fri Aug 29 15:54:11 EDT 2025 Tue Jul 01 00:59:27 EDT 2025 Thu Apr 24 22:57:59 EDT 2025 Thu Aug 27 22:10:49 EDT 2020 |
| IsPeerReviewed | true |
| IsScholarly | true |
| Issue | 2 |
| Keywords | METAL-FREE SYNTHESIS CASCADE REACTIONS S BOND FORMATION COUPLING REACTIONS DERIVATIVES 2-AMINOBENZOTHIAZOLES CYCLIZATION |
| Language | English |
| License | https://doi.org/10.15223/policy-029 https://doi.org/10.15223/policy-037 https://doi.org/10.15223/policy-045 |
| LinkModel | DirectLink |
| LogoURL | https://exlibris-pub.s3.amazonaws.com/fromwos-v2.jpg |
| MergedId | FETCHMERGED-LOGICAL-a366t-4a73ba4b3600f5e98928ab4fec66a900c893a3b0cf069ef57b2b13331a6c84373 |
| Notes | ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23 |
| ORCID | 0000-0002-3354-8318 |
| PMID | 31845809 |
| PQID | 2327932277 |
| PQPubID | 23479 |
| PageCount | 8 |
| ParticipantIDs | pubmed_primary_31845809 proquest_miscellaneous_2400470220 proquest_miscellaneous_2327932277 crossref_citationtrail_10_1021_acs_joc_9b02543 acs_journals_10_1021_acs_joc_9b02543 webofscience_primary_000508468900018 webofscience_primary_000508468900018CitationCount crossref_primary_10_1021_acs_joc_9b02543 |
| ProviderPackageCode | JG~ 55A AABXI GNL VF5 7~N ACJ VG9 W1F ACS AEESW AFEFF .K2 ABMVS ABUCX IH9 BAANH AQSVZ ED~ UI2 CITATION AAYXX |
| PublicationCentury | 2000 |
| PublicationDate | 2020-01-17 |
| PublicationDateYYYYMMDD | 2020-01-17 |
| PublicationDate_xml | – month: 01 year: 2020 text: 2020-01-17 day: 17 |
| PublicationDecade | 2020 |
| PublicationPlace | WASHINGTON |
| PublicationPlace_xml | – name: WASHINGTON – name: United States |
| PublicationTitle | Journal of organic chemistry |
| PublicationTitleAbbrev | J ORG CHEM |
| PublicationTitleAlternate | J. Org. Chem |
| PublicationYear | 2020 |
| Publisher | American Chemical Society Amer Chemical Soc |
| Publisher_xml | – name: American Chemical Society – name: Amer Chemical Soc |
| References | ref17/cit17b ref17/cit17d ref3/cit3 ref17/cit17a ref13/cit13a ref13/cit13b ref13/cit13c ref13/cit13d ref12/cit12d ref13/cit13e ref12/cit12c ref13/cit13f Zotta V. (ref17/cit17c) 1982; 40 ref12/cit12b ref12/cit12a ref8/cit8 ref2/cit2 ref5/cit5b ref5/cit5c ref5/cit5a ref16/cit16c ref16/cit16b ref16/cit16a ref19/cit19 ref7/cit7e ref7/cit7d ref7/cit7c ref7/cit7b ref7/cit7a ref5/cit5f ref5/cit5g ref5/cit5d ref5/cit5e ref18/cit18 ref15/cit15a ref9/cit9c ref9/cit9b ref9/cit9a ref11/cit11 ref15/cit15b ref15/cit15c ref10/cit10a ref10/cit10b ref6/cit6d ref14/cit14a ref14/cit14c ref14/cit14b ref14/cit14d ref4/cit4 ref6/cit6a ref1/cit1 ref6/cit6b ref6/cit6c Ashenhurst, JA (WOS:000274072100013) 2010; 39 Chu, L (WOS:000326774300026) 2013; 135 Sharma, S (WOS:000369771800004) 2016; 18 Shimizu, Y (WOS:000274571500018) 2010; 49 Liu, C (WOS:000366005400002) 2015; 115 Wang, G. (000508468900018.40) 2016; 19 Kozmin, SA (WOS:000175227600031) 2002; 124 Rosen, BR (WOS:000321298800055) 2013; 52 Hajipour, AR (WOS:000343951600017) 2014; 25 Chang, CZ (WOS:000404588800010) 2017; 47 Xu, W (WOS:000416531700007) 2017; 38 Strukil, V (WOS:000307785100017) 2012; 14 Liu, X (WOS:000413162300012) 2017; 2017 Kharbanda, C (WOS:000344471800010) 2014; 22 Thiel, OR (WOS:000255339600026) 2008; 73 Gao, MY (WOS:000453910400012) 2018; 2018 Chang, CZ (WOS:000449443200056) 2018; 83 Shen, C (WOS:000304919200030) 2012; 3 Praveen, C (WOS:000253432600009) 2008; 64 Wang, HB (WOS:000297513300018) 2012; 48 Cao, Q (WOS:000416042700010) 2017 Yoshida, M (WOS:000230337100001) 2005; 15 McCutcheon, DC (WOS:000303696200008) 2012; 134 Dong, ZB (WOS:000414723900052) 2017; 19 Zhang, SB (WOS:000454567900008) 2018; 83 Xu, W (WOS:000406066800004) 2017; 49 Shavaleev, NM (WOS:000267507400071) 2009; 48 He, YM (WOS:000378715600024) 2016; 52 Guntreddi, T (WOS:000349942600054) 2015; 17 Zotta, V. (000508468900018.53) 1982; 40 Zeng, MT (WOS:000457758900002) 2017; 1 Gutekunst, WR (WOS:000288609400011) 2011; 40 Nicolaou, KC (WOS:000242288900003) 2006; 45 Zhang, XY (WOS:000287092500025) 2011; 13 Joyce, LL (WOS:000220108100045) 2004 Noolvi, MN (WOS:000307920600047) 2012; 54 Folgueiras-Amador, AA (WOS:000419623600029) 2018; 24 Liu, X (WOS:000447118100022) 2018; 83 Cheng, JL (WOS:000350329300039) 2015; 119 YOSHINO, K (WOS:A1989AL81000025) 1989; 26 Soleiman-Beigi, M (WOS:000361182900006) 2015; 26 Yin, YZ (WOS:000430654300012) 2018; 360 Zhang, YG (WOS:000248929400003) 2007; 9 Chugunova, E (WOS:000351646100036) 2015; 93 Zhu, H (WOS:000449649100011) 2018; 2018 Inamoto, K (WOS:000260922500013) 2008; 10 Bahrami, K (WOS:000258908000047) 2008; 73 Joyce, LL (WOS:000267400100020) 2009; 11 Soleiman-Beigi, M (WOS:000352796300009) 2015; 26 Yao, S (WOS:000251614900079) 2007; 9 Xu, YS (WOS:000411304500037) 2017; 82 NICOLAOU, KC (WOS:A1994MW68800049) 1994; 367 Liu, X (WOS:000417758700009) 2017; 19 |
| References_xml | – ident: ref5/cit5b doi: 10.1039/B311591G – ident: ref13/cit13d doi: 10.1021/acs.joc.8b02011 – ident: ref5/cit5d doi: 10.1039/C7GC02311A – ident: ref19/cit19 doi: 10.1039/C6CC04394A – ident: ref7/cit7d doi: 10.1002/chem.201705016 – ident: ref9/cit9a doi: 10.1021/ol900958z – ident: ref17/cit17a doi: 10.3184/174751917X14931424175476 – ident: ref17/cit17b doi: 10.1080/00397911.2017.1324033 – ident: ref7/cit7a doi: 10.1021/jp511578v – ident: ref6/cit6b doi: 10.1016/j.ejmech.2012.05.028 – ident: ref6/cit6c doi: 10.1016/j.bmcl.2005.05.077 – ident: ref3/cit3 doi: 10.1080/17415993.2017.1337771 – ident: ref5/cit5e doi: 10.1021/jo8010232 – ident: ref5/cit5f doi: 10.1021/ol7026366 – ident: ref14/cit14d doi: 10.1021/ja017863s – ident: ref6/cit6a doi: 10.1016/j.ejmech.2015.02.023 – ident: ref15/cit15b doi: 10.1021/ja408864c – ident: ref7/cit7e doi: 10.1021/acs.joc.7b01683 – ident: ref13/cit13c doi: 10.1055/s-0036-1588835 – ident: ref14/cit14c doi: 10.1002/anie.200601872 – ident: ref5/cit5c doi: 10.1021/ja301493d – ident: ref13/cit13b doi: 10.1002/ejoc.201701081 – ident: ref7/cit7b doi: 10.1021/ic9005136 – ident: ref4/cit4 doi: 10.1021/jo8002216 – ident: ref9/cit9c doi: 10.1055/s-0036-1590200 – ident: ref16/cit16b doi: 10.1002/ejoc.201801271 – ident: ref13/cit13e doi: 10.1021/acs.joc.8b01644 – ident: ref14/cit14a doi: 10.1038/367630a0 – ident: ref11/cit11 doi: 10.1039/C1CC16184A – ident: ref12/cit12d doi: 10.1021/ol071248x – ident: ref2/cit2 doi: 10.1039/B907809F – ident: ref5/cit5g doi: 10.1016/j.tet.2008.01.004 – ident: ref12/cit12c doi: 10.1055/s-0034-1380141 – ident: ref10/cit10a doi: 10.1021/acs.orglett.5b03185 – ident: ref12/cit12b doi: 10.1002/hc.21267 – ident: ref1/cit1 doi: 10.1021/cr500431s – ident: ref16/cit16c doi: 10.1021/acs.orglett.6b03385 – ident: ref14/cit14b doi: 10.1002/anie.200906678 – ident: ref16/cit16a doi: 10.1002/adsc.201701506 – ident: ref13/cit13f doi: 10.1021/acs.joc.8b02136 – ident: ref6/cit6d doi: 10.1016/j.bmc.2014.09.028 – ident: ref5/cit5a doi: 10.1002/jhet.5570260425 – ident: ref7/cit7c doi: 10.1021/acs.orglett.5b00079 – ident: ref9/cit9b doi: 10.1039/c2sc20248d – ident: ref15/cit15a doi: 10.1039/c0cs00182a – ident: ref13/cit13a doi: 10.1021/acs.orglett.7b02911 – ident: ref10/cit10b doi: 10.1039/C0GC00418A – ident: ref18/cit18 doi: 10.1002/ejoc.201801122 – ident: ref8/cit8 doi: 10.1021/ol802033p – ident: ref17/cit17d doi: 10.1039/c2gc35799b – volume: 40 start-page: 129 year: 1982 ident: ref17/cit17c publication-title: Farmacia (Bucharest) – ident: ref15/cit15c doi: 10.1002/anie.201303838 – ident: ref12/cit12a doi: 10.1016/j.cclet.2014.05.015 – volume: 64 start-page: 2369 year: 2008 ident: WOS:000253432600009 article-title: Oxidative cyclization of thiophenolic and phenolic Schiff's bases promoted by PCC: a new oxidant for 2-substituted benzothiazoles and benzoxazoles publication-title: TETRAHEDRON doi: 10.1016/j.tet.2008.01.004 – volume: 22 start-page: 5804 year: 2014 ident: WOS:000344471800010 article-title: Synthesis and evaluation of pyrazolines bearing benzothiazole as anti-inflammatory agents publication-title: BIOORGANIC & MEDICINAL CHEMISTRY doi: 10.1016/j.bmc.2014.09.028 – volume: 3 start-page: 2388 year: 2012 ident: WOS:000304919200030 article-title: A concise, efficient synthesis of sugar-based benzothiazoles through chemoselective intramolecular C-S coupling publication-title: CHEMICAL SCIENCE doi: 10.1039/c2sc20248d – volume: 54 start-page: 447 year: 2012 ident: WOS:000307920600047 article-title: Benzothiazoles: Search for anticancer agents publication-title: EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY doi: 10.1016/j.ejmech.2012.05.028 – volume: 2018 start-page: 5711 year: 2018 ident: WOS:000449649100011 article-title: Copper(II)-Promoted Cascade Synthesis of 2-Aminobenzothiazoles Starting from 2-Iodoanilines and Sodium Dithiocarbamates publication-title: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY doi: 10.1002/ejoc.201801122 – volume: 19 start-page: 5916 year: 2017 ident: WOS:000414723900052 article-title: Copper-Catalyzed C(sp(2))-S Coupling Reactions for the Synthesis of Aryl Dithiocarbamates with Thiuram Disulfide Reagents publication-title: ORGANIC LETTERS doi: 10.1021/acs.orglett.7b02911 – volume: 82 start-page: 9637 year: 2017 ident: WOS:000411304500037 article-title: Metal-Free Synthesis of 2-Aminobenzothiazoles via Iodine-Catalyzed and Oxygen-Promoted Cascade Reactions of Isothiocyanatobenzenes with Amines publication-title: JOURNAL OF ORGANIC CHEMISTRY doi: 10.1021/acs.joc.7b01683 – volume: 134 start-page: 7604 year: 2012 ident: WOS:000303696200008 article-title: Expedient Synthesis of Electronically Modified Luciferins for Bioluminescence Imaging publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/ja301493d – volume: 83 start-page: 13530 year: 2018 ident: WOS:000449443200056 article-title: Copper-Catalyzed and Air-Mediated Mild Cross-Dehydrogenative Coupling of Aryl Thioureas and Dialkyl H-Phosphonates: The Synthesis of Thiophosphonates publication-title: JOURNAL OF ORGANIC CHEMISTRY doi: 10.1021/acs.joc.8b02011 – volume: 10 start-page: 5147 year: 2008 ident: WOS:000260922500013 article-title: Palladium-Catalyzed Synthesis of 2-Substituted Benzothiazoles via a C-H Functionalization/Intramolecular C-S Bond Formation Process publication-title: ORGANIC LETTERS doi: 10.1021/ol802033p – volume: 49 start-page: 3084 year: 2017 ident: WOS:000406066800004 article-title: Palladium-Catalyzed Synthesis of 2-Aminobenzothiazoles through Tandem Reaction publication-title: SYNTHESIS-STUTTGART doi: 10.1055/s-0036-1588835 – volume: 9 start-page: 5645 year: 2007 ident: WOS:000251614900079 article-title: A new water-soluble near-neutral ratiometric fluorescent pH indicator publication-title: ORGANIC LETTERS doi: 10.1021/ol7026366 – volume: 19 start-page: 110 year: 2016 ident: 000508468900018.40 article-title: Synthesis of δ-and a-Carbolines via Nickel-Catalyzed [2+2+2] Cycloaddition of Functionalized Alkyne-Nitriles with Alkynes publication-title: Org. Lett. – volume: 38 start-page: 644 year: 2017 ident: WOS:000416531700007 article-title: Metal-free or transition-metal-catalyzed one-pot synthesis of 2-aminobenzothiazoles publication-title: JOURNAL OF SULFUR CHEMISTRY doi: 10.1080/17415993.2017.1337771 – volume: 48 start-page: 76 year: 2012 ident: WOS:000297513300018 article-title: Fe-catalysed oxidative C-H functionalization/C-S bond formation publication-title: CHEMICAL COMMUNICATIONS doi: 10.1039/c1cc16184a – start-page: 301 year: 2017 ident: WOS:000416042700010 article-title: Facile synthesis of substituted arylthioureas in the presence of sodium hydride publication-title: JOURNAL OF CHEMICAL RESEARCH doi: 10.3184/174751917X14931424175476 – volume: 17 start-page: 976 year: 2015 ident: WOS:000349942600054 article-title: Elemental Sulfur Mediated Decarboxylative Redox Cyclization Reaction of o-Chloronitroarenes and Arylacetic Acids publication-title: ORGANIC LETTERS doi: 10.1021/acs.orglett.5b00079 – volume: 45 start-page: 7134 year: 2006 ident: WOS:000242288900003 article-title: Cascade reactions in total synthesis publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION doi: 10.1002/anie.200601872 – volume: 40 start-page: 1976 year: 2011 ident: WOS:000288609400011 article-title: C-H functionalization logic in total synthesis publication-title: CHEMICAL SOCIETY REVIEWS doi: 10.1039/c0cs00182a – volume: 73 start-page: 3508 year: 2008 ident: WOS:000255339600026 article-title: Practical synthesis of a vanilloid receptor-1 antagonist publication-title: JOURNAL OF ORGANIC CHEMISTRY doi: 10.1021/jo8002216 – volume: 25 start-page: 1382 year: 2014 ident: WOS:000343951600017 article-title: Highly efficient and magnetically separable nano-CuFe2O4 catalyzed S-arylation of thiourea by aryl/heteroaryl halides publication-title: CHINESE CHEMICAL LETTERS doi: 10.1016/j.cclet.2014.05.015 – volume: 119 start-page: 4242 year: 2015 ident: WOS:000350329300039 article-title: Comprehensive Studies on Excited-State Proton Transfer of a Series of 2-(2 '-Hydroxyphenyl)benzothiazole Derivatives: Synthesis, Optical Properties, and Theoretical Calculations publication-title: JOURNAL OF PHYSICAL CHEMISTRY C doi: 10.1021/jp511578v – volume: 360 start-page: 1639 year: 2018 ident: WOS:000430654300012 article-title: Ni-Catalyzed C-F Bond Functionalization of Unactivated Aryl Fluorides and Corresponding Coupling with Oxazoles publication-title: ADVANCED SYNTHESIS & CATALYSIS doi: 10.1002/adsc.201701506 – volume: 18 start-page: 356 year: 2016 ident: WOS:000369771800004 article-title: Ruthenium Catalyzed Intramolecular C-S Coupling Reactions: Synthetic Scope and Mechanistic Insight publication-title: ORGANIC LETTERS doi: 10.1021/acs.orglett.5b03185 – start-page: 446 year: 2004 ident: WOS:000220108100045 article-title: Copper- and palladium-catalyzed intramolecular C-S bond formation: a convenient synthesis of 2-aminobenzothiazoles publication-title: CHEMICAL COMMUNICATIONS doi: 10.1039/b311591g – volume: 47 start-page: 1262 year: 2017 ident: WOS:000404588800010 article-title: Copper-catalyzed tandem reaction of 2-haloanilines with thiocarbamoyl chloride: Synthesis of 2-aminobenzothiazoles publication-title: SYNTHETIC COMMUNICATIONS doi: 10.1080/00397911.2017.1324033 – volume: 83 start-page: 14933 year: 2018 ident: WOS:000454567900008 article-title: One-Pot Synthesis of 2-Benzyl/2-Allyl-Substituted Thiobenzoazoles Using Transition-Metal-Free Conditions in Water publication-title: JOURNAL OF ORGANIC CHEMISTRY doi: 10.1021/acs.joc.8b02136 – volume: 19 start-page: 5591 year: 2017 ident: WOS:000417758700009 article-title: An environmentally benign and efficient synthesis of substituted benzothiazole-2-thiols, benzoxazole-2-thiols, and benzimidazoline-2-thiones in water publication-title: GREEN CHEMISTRY doi: 10.1039/c7gc02311a – volume: 15 start-page: 3328 year: 2005 ident: WOS:000230337100001 article-title: Synthesis and biological evaluation of benzothiazole derivatives as potent antitumor agents publication-title: BIOORGANIC & MEDICINAL CHEMISTRY LETTERS doi: 10.1016/j.bmcl.2005.05.077 – volume: 1 start-page: 1 year: 2017 ident: WOS:000457758900002 article-title: Iodobenzene-Promoted Pd-Catalysed ortho-Directed C-H Activation: The Synthesis of Benzothiazoles via Intramolecular Coupling publication-title: SYNOPEN doi: 10.1055/s-0036-1590200 – volume: 13 start-page: 413 year: 2011 ident: WOS:000287092500025 article-title: An economically and environmentally sustainable synthesis of 2-aminobenzothiazoles and 2-aminobenzoxazoles promoted by water publication-title: GREEN CHEMISTRY doi: 10.1039/c0gc00418a – volume: 48 start-page: 6178 year: 2009 ident: WOS:000267507400071 article-title: Benzothiazole- and Benzoxazole-Substituted Pyridine-2-Carboxylates as Efficient Sensitizers of Europium Luminescence publication-title: INORGANIC CHEMISTRY doi: 10.1021/ic9005136 – volume: 9 start-page: 3495 year: 2007 ident: WOS:000248929400003 article-title: The first n-heterocyclic carbene-based nickel catalyst for C-S coupling publication-title: ORGANIC LETTERS doi: 10.1021/ol071248x – volume: 115 start-page: 12138 year: 2015 ident: WOS:000366005400002 article-title: Oxidative Coupling between Two Hydrocarbons: An Update of Recent C-H Functionalizations publication-title: CHEMICAL REVIEWS doi: 10.1021/cr500431s – volume: 367 start-page: 630 year: 1994 ident: WOS:A1994MW68800049 article-title: TOTAL SYNTHESIS OF TAXOL publication-title: NATURE – volume: 49 start-page: 1103 year: 2010 ident: WOS:000274571500018 article-title: Catalytic Asymmetric Total Synthesis of ent-Hyperforin publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION doi: 10.1002/anie.200906678 – volume: 124 start-page: 4628 year: 2002 ident: WOS:000175227600031 article-title: An efficient approach to Aspidosperma alkaloids via [4+2] cycloadditions of aminosiloxydienes: Stereocontrolled total synthesis of (+/-)-tabersonine. Gram-scale catalytic asymmetric syntheses of (+)-tabersonine and (+)-16-methoxytabersonine. Asymmetric syntheses of (+)-aspidospermidine and (-)-quebrachamine publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/ja017863s – volume: 52 start-page: 8444 year: 2016 ident: WOS:000378715600024 article-title: A metal-free synthesis of 2-aminobenzothiazoles through aminyl radical addition to aryl isothiocyanates publication-title: CHEMICAL COMMUNICATIONS doi: 10.1039/c6cc04394a – volume: 11 start-page: 2792 year: 2009 ident: WOS:000267400100020 article-title: Heterocycle Formation via Palladium-Catalyzed Intramolecular Oxidative C-H Bond Functionalization: An Efficient Strategy for the Synthesis of 2-Aminobenzothiazoles publication-title: ORGANIC LETTERS doi: 10.1021/ol900958z – volume: 52 start-page: 7317 year: 2013 ident: WOS:000321298800055 article-title: C-H Functionalization Logic Enables Synthesis of (+)-Hongoquercin A and Related Compounds publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION doi: 10.1002/anie.201303838 – volume: 40 start-page: 129 year: 1982 ident: 000508468900018.53 article-title: Studies in urea and thiourea series. III. New Di-and Trisubstituted Derivatives publication-title: Farmacia (Bucharest) – volume: 26 start-page: 1039 year: 1989 ident: WOS:A1989AL81000025 article-title: ORGANIC PHOSPHORUS-COMPOUNDS .3. SYNTHESIS OF 5-FLUOROSUBSTITUTED BENZOTHIAZOLYLBENZYLPHOSPHONATES publication-title: JOURNAL OF HETEROCYCLIC CHEMISTRY – volume: 24 start-page: 487 year: 2018 ident: WOS:000419623600029 article-title: Catalyst- and Supporting-Electrolyte-Free Electrosynthesis of Benzothiazoles and Thiazolopyridines in Continuous Flow publication-title: CHEMISTRY-A EUROPEAN JOURNAL doi: 10.1002/chem.201705016 – volume: 14 start-page: 2462 year: 2012 ident: WOS:000307785100017 article-title: A model for a solvent-free synthetic organic research laboratory: click-mechanosynthesis and structural characterization of thioureas without bulk solvents publication-title: GREEN CHEMISTRY doi: 10.1039/c2gc35799b – volume: 2017 start-page: 5795 year: 2017 ident: WOS:000413162300012 article-title: Nickel-Catalyzed C-S Coupling: Synthesis of Diaryl Sulfides Starting from Phenyldithiocarbamates and Iodobenzenes publication-title: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY doi: 10.1002/ejoc.201701081 – volume: 2018 start-page: 6693 year: 2018 ident: WOS:000453910400012 article-title: Synthesis of Phenyl Dithiocarbamates Starting from Sodium Dialkyldithiocarbamates and Aryl Boronic Acids: a Copper Catalyzed S-Arylation publication-title: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY doi: 10.1002/ejoc.201801271 – volume: 26 start-page: 911 year: 2015 ident: WOS:000352796300009 article-title: A Novel Nickel-Catalyzed Domino Method for the Direct Synthesis of Symmetrical Disulfides Using Potassium 5-Methyl-1,3,4-oxadiazole-2-thiolate as a Sulfurating Reagent publication-title: SYNLETT doi: 10.1055/s-0034-1380141 – volume: 83 start-page: 11703 year: 2018 ident: WOS:000447118100022 article-title: Copper(I)-Catalyzed Tandem One-Pot Synthesis of 2-Arylthiobenzothiazoles and 2-Arylthiobenzoxazoles in Water publication-title: JOURNAL OF ORGANIC CHEMISTRY doi: 10.1021/acs.joc.8b01644 – volume: 26 start-page: 355 year: 2015 ident: WOS:000361182900006 article-title: Ni-Catalyzed Cross-Coupling Reaction: The Direct Synthesis of Symmetrical Disulfanes from Aryl and Primary Alkyl Halides publication-title: HETEROATOM CHEMISTRY doi: 10.1002/hc.21267 – volume: 39 start-page: 540 year: 2010 ident: WOS:000274072100013 article-title: Intermolecular oxidative cross-coupling of arenes publication-title: CHEMICAL SOCIETY REVIEWS doi: 10.1039/b907809f – volume: 93 start-page: 349 year: 2015 ident: WOS:000351646100036 article-title: Synthesis and antimicrobial activity of novel structural hybrids of benzofuroxan and benzothiazole derivatives publication-title: EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY doi: 10.1016/j.ejmech.2015.02.023 – volume: 135 start-page: 16344 year: 2013 ident: WOS:000326774300026 article-title: Pd-Catalyzed Enantioselective C-H Iodination: Asymmetric Synthesis of Chiral Diarylmethylamines publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/ja408864c – volume: 73 start-page: 6835 year: 2008 ident: WOS:000258908000047 article-title: Mild and highly efficient method for the synthesis of 2-arylbenzimidazoles and 2-arylbenzothiazoles publication-title: JOURNAL OF ORGANIC CHEMISTRY doi: 10.1021/jo8010232 |
| SSID | ssj0000555 |
| Score | 2.489953 |
| Snippet | A highly efficient synthetic method for the preparation of 2-aminobenzothiazoles starting from arylthioureas has been reported. By using a nickel catalyst,... |
| Source | Web of Science |
| SourceID | proquest pubmed webofscience crossref acs |
| SourceType | Aggregation Database Index Database Enrichment Source Publisher |
| StartPage | 493 |
| SubjectTerms | carbon-hydrogen bond activation catalysts catalytic activity chemical bonding chemical reactions chemical structure Chemistry Chemistry, Organic nickel organic chemistry organic compounds Physical Sciences Science & Technology |
| Title | A Mild Synthesis of 2‑Substituted Benzothiazoles via Nickel-Catalyzed Intramolecular Oxidative C–H Functionalization |
| URI | http://dx.doi.org/10.1021/acs.joc.9b02543 http://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcApp=Summon&SrcAuth=ProQuest&DestApp=WOS&DestLinkType=FullRecord&UT=000508468900018 https://www.ncbi.nlm.nih.gov/pubmed/31845809 https://www.proquest.com/docview/2327932277 https://www.proquest.com/docview/2400470220 |
| Volume | 85 |
| WOS | 000508468900018 |
| WOSCitedRecordID | wos000508468900018 |
| hasFullText | 1 |
| inHoldings | 1 |
| isFullTextHit | |
| isPrint | |
| link | http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwjV1Lb9QwELagHODCG7q8ZKQeuDgkfudYIlYLUuFQKvUW2Y4jhS5Z1GRRu6f-BcQ_7C_Bk2RTYCn0mowT2R7PfB57vkFox2vtrVCUMGck4dQzokvvCVeuKFhqRckh33nvg5wd8PeH4vCCLPrPE3yavDauiT4vXJTaLnH7OrpBZVjCgIKy_QujK4QYicGpZCOLz8YHwA255nc3tIEt_-qGOpczvdNf1mo6pkK4aXIULVsbudUmj-P_e3MX3R6AJ97tNeUeuubr--hmtq739gCd7OK9al7g_dM6gMKmavCixPT87DvYlv5CQYHf-HoV5rYyKyCCwt8qg4MuHfk5ySAOdLoKMu8gXvxlXXYXfzypio5dHGfnZz9meBo8aR-AHFJAH6KD6dtP2YwMdRmIYVK2hBvFrOGWBbBUCp_qlGpjeemdlCaNYxcwkGE2dmUsU18KZakNW2GWGOk0UCk9Qlv1ovbbCCsdTExR2MLB1qmwqSyBkE0Ln1jFuJqgnTBi-bCumrw7MqdJ3j90-TCMExStZzN3A7c5lNiYX97g1djga0_rcbnoy7V65GFG4DzF1H6xbPIARoN1o1Spf8iAjVSQzjxBj3vdGn8YzCkXOk5DJ39VtvF9R84T8KGGwq6JnqDkKmLZ0H_gNGifXG38nqJbFOIIcUIS9QxttcdL_zyArda-6JbZTxoQJd4 |
| linkProvider | American Chemical Society |
| linkToHtml | http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwlV1Jb9QwFLZKOZRLy94pm5F64JIhseMlxyFiNIVOEWor9RbZjiOFTjMVyaB2Tv0LiH_YX8JztgKlqFwd2_Hy_N7n5X0PoW0rpdVMEI8axb2QWOrJzFovFCZNaaRZFjp_5-kenxyGH47Y0QryO18YaEQJNZX1Jf4Vu0Dw1qV9mZthpGv_7TvoLkAR4mR6FO9f6V7GWM8PTjjtyXyuVeCskSl_t0bXIOZfrVFtecYb6HPf5vrByfFwUemhWf5B5_g_nbqP1lsYikeN3DxAK7Z4iNbiLvrbI3Q2wtN8luL98wIgYpmXeJ5hcnnx3Wma5nlBit_ZYgkznaulo4XC33KFQbKO7cyL3anQ-RLy7LjT45MuCC_-dJanNdc4ji8vfkzwGOxqcxzZOoQ-Rofj9wfxxGujNHiKcl55oRJUq1BTgE4Zs5GMiFQ6zKzhXEW-bwARKap9k_k8shkTmmjYGNNAcSMdsdITtFrMC7uJsJCgcNJUp8ZtpFId8czRs0lmAy1oKAZoG0YsaVdZmdQX6CRImkSTtMM4QMNuUhPTMp27gBuzmwu86QucNiQfN2d93UlJAjPibldUYeeLMgFoCrqOECH-kcdpTOGcmwfoaSNi_Q9BuYZM-hF08leZ67_XVD2AFqUL8xrIAQpuky1u--8YDqqt243fK7Q2OZjuJrs7ex-foXvEnTD4gReI52i1-rqwLwCGVfplvfJ-AjFxLj8 |
| linkToPdf | http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwlV1Lb9QwELagSMCF8izL00g9cMmS2PEjxyWw2gItSGWl3iK_IqVdshXJonZP_QuIf9hfUk-SDY9SVK6O7fgxnhnPeL5BaNNJ6TQTJKBG8SAmjgYydy6IhbGWJprlMcQ7b-_wyTR-t8f2uqAwiIXxg6h8T1XjxIdTfWjzDmEgegXl-3MzTHQTw30VXQOnHdD1KN39yX8ZYz1GOOG0B_Q51wFIJFP9LpHOqZl_lUiN9Bmvo2k_7ubRycFwUeuhWf4B6fi_E7uNbnXqKB619HMHXXHlXXQjXWWBu4eORni7mFm8e1x6VbEqKjzPMTk9-Q4cp31mYPFrVy79jhdqCfBQ-FuhsKewAzcLUrAOHS99nS2wIn9ZJePFH48K22CO4_T05McEj718bc2SXWDofTQdv_2cToIuW0OgKOd1ECtBtYo19SpUzlwiEyKVjnNnOFdJGBqvGSmqQ5OHPHE5E5pof0GmkeJGAsDSA7RWzkv3EGEhPeOxVlsDFyqrE54DTJtkLtKCxmKANv2KZd1pq7LGkU6irC00WbeMAzRcbWxmOsRzSLwxu7jBy77BYQv2cXHVFytKyfyOgJdFlW6-qDKvonqeR4gQ_6gDnFNAkPMAbbRk1v_QM9mYyTDxk_yV7vrvDWSP1xolpHuN5ABFl6mWdvMHpIP60eXW7zm6_unNOPuwtfP-MbpJwNAQRkEknqC1-uvCPfXaWK2fNYfvDNTjMMI |
| 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=A+Mild+Synthesis+of+2-Substituted+Benzothiazoles+via+Nickel-Catalyzed+Intramolecular+Oxidative+C%E2%80%93H+Functionalization&rft.jtitle=Journal+of+organic+chemistry&rft.au=Gao%2C+Ming-Yuan&rft.au=Li%2C+Jing-Hang&rft.au=Zhang%2C+Shi-Bo&rft.au=Chen%2C+Li-Jun&rft.date=2020-01-17&rft.issn=1520-6904&rft.volume=85&rft.issue=2+p.493-500&rft.spage=493&rft.epage=500&rft_id=info:doi/10.1021%2Facs.joc.9b02543&rft.externalDBID=NO_FULL_TEXT |
| thumbnail_l | http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/lc.gif&issn=0022-3263&client=summon |
| thumbnail_m | http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/mc.gif&issn=0022-3263&client=summon |
| thumbnail_s | http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/sc.gif&issn=0022-3263&client=summon |