CuO-Promoted Construction of N-2-Aryl-Substituted-1,2,3-Triazoles via Azide-Chalcone Oxidative Cycloaddition and Post-Triazole Arylation
An efficient one-pot three-component stepwise approach for the synthesis of N-2-aryl-substituted-1,2,3-triazoles has been developed. By using this azide-chalcone oxidative cycloaddition and post-triazole arylation, a series of N-2-aryl-substituted-1,2,3-triazoles are readily prepared under mild cond...
Saved in:
| Published in | Organic letters Vol. 14; no. 1; pp. 26 - 29 |
|---|---|
| Main Authors | , , , , , , |
| Format | Journal Article |
| Language | English |
| Published |
WASHINGTON
American Chemical Society
06.01.2012
Amer Chemical Soc |
| Subjects | |
| Online Access | Get full text |
Cover
Loading…
| Abstract | An efficient one-pot three-component stepwise approach for the synthesis of N-2-aryl-substituted-1,2,3-triazoles has been developed. By using this azide-chalcone oxidative cycloaddition and post-triazole arylation, a series of N-2-aryl-substituted-1,2,3-triazoles are readily prepared under mild conditions in excellent yields and high regioselectivity. Both the catalyst and substrates are readily available. |
|---|---|
| AbstractList | An efficient one-pot three-component stepwise approach for the synthesis of N-2-aryl-substituted-1,2,3-triazoles has been developed. By using this azide-chalcone oxidative cycloaddition and post-triazole arylation, a series of N-2-aryl-substituted-1,2,3-triazoles are readily prepared under mild conditions in excellent yields and high regioselectivity. Both the catalyst and substrates are readily available. |
| Author | Li, Jihui Meng, Xu Chen, Baohua Zhang, Yuanqing Zhao, Mingming Li, Xiaolong Chen, Jinying |
| Author_xml | – sequence: 1 givenname: Yuanqing surname: Zhang fullname: Zhang, Yuanqing – sequence: 2 givenname: Xiaolong surname: Li fullname: Li, Xiaolong – sequence: 3 givenname: Jihui surname: Li fullname: Li, Jihui – sequence: 4 givenname: Jinying surname: Chen fullname: Chen, Jinying – sequence: 5 givenname: Xu surname: Meng fullname: Meng, Xu – sequence: 6 givenname: Mingming surname: Zhao fullname: Zhao, Mingming – sequence: 7 givenname: Baohua surname: Chen fullname: Chen, Baohua email: chbh@lzu.edu.cn |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/22133007$$D View this record in MEDLINE/PubMed |
| BookMark | eNqNkMtuFDEQRS0URB6w4AdQbxBCxFC2p6c9y1GLlxRlIiX7lscuC0c9dvAjZPIF-Ww8mdArFtlUlcrnXpXvMTnwwSMhbxl8ZsDZlzBy4B2T5gU5Yi0XtIOWH0zzHA7JcUrXAKxuFq_IIedMCIDuiDz0ZUUvYtiEjKbpg085Fp1d8E2wzTnldBm3I70s65RdLhWi7JSfCnoVnboPI6bm1qlmee8M0v6XGnU9rVndOaOyu8Wm3-oxKGPco6XyprkIKU_qZueudm-vyUurxoRvnvoJufz29ar_Qc9W33_2yzOqhIRMFed8rpjtWskQFtZwydba6HYurGGA9cd61kkLaLEuhFCzWhGFEjNtxQn5sHe9ieF3wZSHjUsax1F5DCUNCzabd4KLtpIf96SOIaWIdriJbqPidmAw7FIfptQr--7Jtaw3aCbyX8wV-LQH_uA62KQdeo0TBgB8ISWXbZ1AVlo-n-5dfsyvD8XnKn2_lyqdhutQoq9Z_ufivz4ArJw |
| CitedBy_id | crossref_primary_10_1002_chem_201202215 crossref_primary_10_1021_ol501547p crossref_primary_10_1016_j_tetlet_2019_151422 crossref_primary_10_1002_slct_201800816 crossref_primary_10_1016_j_tet_2014_07_032 crossref_primary_10_1016_j_tetlet_2023_154599 crossref_primary_10_2174_1570179417666191223152643 crossref_primary_10_1039_C7NJ03527F crossref_primary_10_1021_acs_orglett_5b02020 crossref_primary_10_1039_c3ra22485f crossref_primary_10_1002_ejoc_202101470 crossref_primary_10_1007_s11164_013_1148_6 crossref_primary_10_1002_cctc_202101926 crossref_primary_10_1021_acs_joc_7b00752 crossref_primary_10_1002_ange_201305970 crossref_primary_10_1039_D3OB00792H crossref_primary_10_1016_j_ijbiomac_2019_03_019 crossref_primary_10_2174_1385272823666191021114906 crossref_primary_10_1039_C4RA09970B crossref_primary_10_1186_s40064_016_3398_4 crossref_primary_10_1070_RCR4450 crossref_primary_10_1016_j_molstruc_2022_133795 crossref_primary_10_1039_D3OB01115A crossref_primary_10_1007_s12039_021_02001_5 crossref_primary_10_1039_D1OB01717A crossref_primary_10_1016_j_molstruc_2015_02_028 crossref_primary_10_1021_acs_orglett_2c00621 crossref_primary_10_1021_acs_orglett_0c00006 crossref_primary_10_1002_cjoc_201700367 crossref_primary_10_1007_s11164_016_2457_3 crossref_primary_10_5155_eurjchem_5_1_85_90_789 crossref_primary_10_1021_acs_joc_0c01433 crossref_primary_10_1021_acs_orglett_9b02140 crossref_primary_10_1016_j_tet_2012_07_008 crossref_primary_10_1007_s11030_021_10257_9 crossref_primary_10_1021_jo300592t crossref_primary_10_1071_CH16540 crossref_primary_10_1002_ejoc_201201587 crossref_primary_10_1002_jhet_4617 crossref_primary_10_1016_j_tetlet_2015_03_019 crossref_primary_10_1039_D3QO01086D crossref_primary_10_1177_1747519820946253 crossref_primary_10_1021_ol300114w crossref_primary_10_1002_anie_201305970 crossref_primary_10_1016_j_tet_2014_09_067 crossref_primary_10_1039_D1CC06477K crossref_primary_10_1002_ejoc_201601121 crossref_primary_10_1016_j_carres_2015_07_004 crossref_primary_10_1002_adsc_201300344 crossref_primary_10_1021_ol503687w crossref_primary_10_1039_C5RA08693K crossref_primary_10_1039_c3oc90009f crossref_primary_10_1021_acs_joc_7b01429 crossref_primary_10_1016_j_tetlet_2021_153440 crossref_primary_10_1002_chin_201220135 crossref_primary_10_1002_ejoc_201800843 crossref_primary_10_1021_acs_joc_8b00107 crossref_primary_10_1016_j_steroids_2022_109133 crossref_primary_10_1002_chem_201903385 crossref_primary_10_1007_s13738_021_02164_5 crossref_primary_10_1039_D1NJ01998H crossref_primary_10_1021_acs_orglett_5b01242 crossref_primary_10_1080_00304948_2024_2334167 crossref_primary_10_1016_j_tetlet_2015_07_016 crossref_primary_10_1039_C5RA27907K crossref_primary_10_1021_acs_joc_8b02476 crossref_primary_10_3389_fchem_2018_00527 crossref_primary_10_1016_j_tet_2015_12_059 crossref_primary_10_3987_REV_13_781 crossref_primary_10_1039_C6CC06194J crossref_primary_10_1002_aoc_3947 crossref_primary_10_1039_C4RA05599C crossref_primary_10_1002_slct_202202354 crossref_primary_10_1007_s10593_016_1821_y crossref_primary_10_3184_174751914X14108592918139 crossref_primary_10_1002_ajoc_201300009 crossref_primary_10_1002_cctc_201700401 crossref_primary_10_1016_j_tetlet_2016_06_004 crossref_primary_10_1039_C5RA16974G crossref_primary_10_1002_adsc_202000970 crossref_primary_10_1002_slct_202202914 crossref_primary_10_1007_s12039_018_1452_1 crossref_primary_10_1002_ajoc_201500390 crossref_primary_10_2174_1385272826666220908120319 crossref_primary_10_1002_cjoc_201600922 crossref_primary_10_1021_acs_joc_9b02865 crossref_primary_10_1002_ejoc_201300924 |
| Cites_doi | 10.1055/s-2007-968007 10.1021/ja044996f 10.1016/j.tetlet.2010.12.053 10.1039/b805328f 10.1021/jp021000j 10.1021/ol802246q 10.1039/c1cc14257g 10.1021/ol800675u 10.1055/s-0030-1258086 10.1021/ol061657d 10.1021/ol901040d 10.1039/b203577d 10.1021/ol102209p 10.1021/jo061688m 10.1016/S0040-4020(03)00621-5 10.1021/ja808622z 10.1021/jo011148j 10.1002/anie.200454078 10.1002/ejoc.201000610 10.1016/j.molstruc.2008.05.028 10.1016/j.tetlet.2007.06.069 10.1021/ol8006748 10.1021/ja034191s 10.1080/00397910600781216 10.1021/ol9019875 10.1021/ol200183b 10.1021/jo00986a048 10.1002/1521-3773(20020715)41:14<2596::AID-ANIE2596>3.0.CO;2-4 10.3987/COM-97-7997 10.1002/cber.19650981228 10.3987/COM-99-8518 10.1016/S0022-1139(02)00103-3 10.1016/S1359-6446(03)02933-7 10.1002/1521-3773(20010601)40:11<2004::AID-ANIE2004>3.0.CO;2-5 10.1016/j.tetlet.2003.10.051 |
| ContentType | Journal Article |
| Copyright | Copyright © 2011 American Chemical Society 2011 American Chemical Society |
| Copyright_xml | – notice: Copyright © 2011 American Chemical Society – notice: 2011 American Chemical Society |
| DBID | 1KM 1KN BLEPL DTL GKHJH NPM AAYXX CITATION 7X8 |
| DOI | 10.1021/ol202718d |
| DatabaseName | Index Chemicus Current Chemical Reactions Web of Science Core Collection Science Citation Index Expanded Web of Science - Science Citation Index Expanded - 2012 PubMed CrossRef MEDLINE - Academic |
| DatabaseTitle | Web of Science PubMed CrossRef MEDLINE - Academic |
| DatabaseTitleList | 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 | 1523-7052 |
| EndPage | 29 |
| ExternalDocumentID | 10_1021_ol202718d 22133007 000298828500008 d273754362 |
| Genre | Journal Article |
| GrantInformation_xml | – fundername: Project of National Science Foundation of P. R. China grantid: J0730425 – fundername: Scientific Research Foundation for the State Education Ministry grantid: 107108 |
| GroupedDBID | - .K2 123 4.4 53G 55A 5VS 7~N AABXI ABFLS ABMVS ABPTK ABUCX ACGFS ACS AEESW AENEX AFEFF ALMA_UNASSIGNED_HOLDINGS AQSVZ BAANH CS3 DU5 DZ EBS ED ED~ F5P GNL IH9 IHE JG JG~ K2 LG6 P2P RNS ROL TN5 UI2 VF5 VG9 W1F X YNT --- -DZ -~X 1KM 1KN 6P2 AAHBH ABJNI ABQRX ADHLV AHGAQ BLEPL CUPRZ DTL GGK GROUPED_WOS_SCIENCE_CITATION_INDEX_EXPANDED NPM AAYXX CITATION 7X8 |
| ID | FETCH-LOGICAL-a380t-a2226a1f7581e09fd281bcdc563fd10e523c478f0efefd133a4d13ee3a34cf3 |
| IEDL.DBID | ACS |
| ISICitedReferencesCount | 97 |
| ISICitedReferencesURI | https://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcApp=Summon&SrcAuth=ProQuest&DestApp=WOS&DestLinkType=CitingArticles&UT=000298828500008 |
| ISSN | 1523-7060 |
| IngestDate | Fri Aug 16 05:53:02 EDT 2024 Fri Aug 23 01:50:29 EDT 2024 Tue Aug 27 13:47:14 EDT 2024 Wed Sep 18 03:51:02 EDT 2024 Tue Sep 17 23:31:00 EDT 2024 Thu Aug 27 13:42:44 EDT 2020 |
| IsPeerReviewed | true |
| IsScholarly | true |
| Issue | 1 |
| Keywords | SODIUM-AZIDE ONE-POT SYNTHESIS TERMINAL ACETYLENES 1,2,3-TRIAZOLES 1,3-DIPOLAR CYCLOADDITION REGIOSELECTIVE SYNTHESIS EFFICIENT SYNTHESIS SOLID-PHASE CLICK-CHEMISTRY ALKYNE CYCLOADDITION |
| Language | English |
| License | 2011 American Chemical Society |
| LinkModel | DirectLink |
| LogoURL | https://exlibris-pub.s3.amazonaws.com/fromwos-v2.jpg |
| MergedId | FETCHMERGED-LOGICAL-a380t-a2226a1f7581e09fd281bcdc563fd10e523c478f0efefd133a4d13ee3a34cf3 |
| Notes | ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23 |
| PMID | 22133007 |
| PQID | 914673235 |
| PQPubID | 23479 |
| PageCount | 4 |
| ParticipantIDs | crossref_primary_10_1021_ol202718d acs_journals_10_1021_ol202718d pubmed_primary_22133007 webofscience_primary_000298828500008 proquest_miscellaneous_914673235 webofscience_primary_000298828500008CitationCount |
| ProviderPackageCode | JG~ 55A AABXI GNL VF5 7~N VG9 W1F ACS AEESW AFEFF .K2 ABMVS ABUCX IH9 BAANH AQSVZ ED~ UI2 |
| PublicationCentury | 2000 |
| PublicationDate | 2012-01-06 |
| PublicationDateYYYYMMDD | 2012-01-06 |
| PublicationDate_xml | – month: 01 year: 2012 text: 2012-01-06 day: 06 |
| PublicationDecade | 2010 |
| PublicationPlace | WASHINGTON |
| PublicationPlace_xml | – name: WASHINGTON – name: United States |
| PublicationTitle | Organic letters |
| PublicationTitleAbbrev | ORG LETT |
| PublicationTitleAlternate | Org. Lett |
| PublicationYear | 2012 |
| Publisher | American Chemical Society Amer Chemical Soc |
| Publisher_xml | – name: American Chemical Society – name: Amer Chemical Soc |
| References | Sreedhar, B (WOS:000248799000025) 2007; 48 NORBEDO I (WOS:000298828500008.21) 2003; 44 Wu, P (WOS:000244333400002) 2007; 40 Aucagne, V (WOS:000240654700031) 2006; 8 Maliakal, A (WOS:000177705000006) 2002; 106 Liu, YX (WOS:000261294300018) 2008; 10 Kamijo, S (WOS:000183814500018) 2003; 125 Majireck, MM (WOS:000241435600057) 2006; 71 Rostovtsev, VV (WOS:000176972000038) 2002; 41 Freeze, S (WOS:000082079900005) 1999; 51 Kolb, HC (WOS:000187217100009) 2003; 8 Louerat, F (WOS:000071802800022) 1998; 48 Wu, P (WOS:000223047200009) 2004; 43 Li, JH (WOS:000279048600005) 2010 Wacharasindhu, S (WOS:000264792900002) 2009; 131 Zanirato, P (WOS:000176095900003) 2002 TANAKA, Y (WOS:A1972N814200048) 1972; 37 Agard, NJ (WOS:000225233600024) 2004; 126 Qian, WY (WOS:000288691600027) 2011; 13 Cohrt, AE (WOS:000284555600015) 2010; 12 Tang, WJ (WOS:000240162600007) 2006; 36 Kolb, HC (WOS:000169168100001) 2001; 40 Kamalraj, VR (WOS:000261711400035) 2008; 892 Li, N (WOS:000287630700008) 2011; 52 Peng, WM (WOS:000177171100016) 2002; 116 Yang, D (WOS:000246701300020) 2007 Tornoe, CW (WOS:000175323600045) 2002; 67 Donohoe, TJ (WOS:000295004300024) 2011; 47 Meng, X (WOS:000283387900010) 2010; 2010 Wang, XJ (WOS:000271097100066) 2009; 11 HUISGEN, R (WOS:A19657049200027) 1965; 98 Shi, F (WOS:000256762100021) 2008; 10 Kalisiak, J (WOS:000257955100001) 2008; 10 Peng, WM (WOS:000183358200018) 2003; 59 Li, JH (WOS:000268138800018) 2009; 11 Chen, YF (WOS:000257552700007) 2008 Kamalraj V. R. (ref6/cit6d) 2008; 892 Donohoe T. J. (ref6/cit6e) 2011 Tornøe C. W. (ref3/cit3a) 2002; 67 Cohrt A. E. (ref1/cit1d) 2011; 12 Kalisiak J. (ref4/cit4c) 2008; 10 Freeze S. (ref5/cit5d) 1999; 51 Peng W. (ref5/cit5a) 2003; 59 Chen Y. (ref4/cit4b) 2008 Liu Y. (ref4/cit4d) 2008; 10 Li J (ref7/cit7b) 2010 Maliakal A. (ref2/cit2a) 2002; 106 Louerat F. (ref5/cit5e) 1998; 48 Zanirato P. (ref5/cit5c) 2002 Li J. (ref7/cit7a) 2009; 11 Tang W. (ref8/cit8) 2006; 36 Rostovtsev V. V. (ref1/cit1b) 2002; 41 Majireck M. M. (ref3/cit3c) 2006; 71 Sreedhar B. (ref3/cit3e) 2007; 48 Wang X. (ref4/cit4e) 2009; 11 Kolb H. C. (ref1/cit1a) 2001; 40 Aucagne V. (ref3/cit3b) 2006; 8 Kamijo S. (ref4/cit4a) 2002; 125 Agard N. J. (ref2/cit2d) 2004; 126 Wu P. (ref2/cit2c) 2004; 43 Meng X. (ref7/cit7c) 2010 Shi F. (ref3/cit3f) 2008; 10 Peng W. (ref5/cit5b) 2002; 116 Li N. (ref7/cit7d) 2011; 52 Qian W. (ref3/cit3g) 2011; 13 Wu P. (ref1/cit1c) 2007; 40 Wacharasindhu S. (ref2/cit2f) 2009; 131 Tanaka Y. (ref6/cit6b) 1972; 37 Yang D. (ref3/cit3d) 2007 Kolb H. C. (ref2/cit2b) 2003; 8 Norbedo I. (ref6/cit6c) 2003; 44 Huisgen R. (ref6/cit6a) 1965; 98 |
| References_xml | – start-page: 278 year: 2007 ident: WOS:000246701300020 article-title: A convenient synthesis of 1,4,5-trisubstituted 1,2,3-triazoles via 1,3-dipolar cycloaddition/coupling of alkynes, phenylboronic acids, and sodium azide catalyzed by Cu(I)/Cu(II) publication-title: SYNLETT doi: 10.1055/s-2007-968007 contributor: fullname: Yang, D – volume: 41 start-page: 2596 year: 2002 ident: WOS:000176972000038 article-title: A stepwise Huisgen cycloaddition process: Copper(I)-catalyzed regioselective "ligation" of azides and terminal alkynes publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION contributor: fullname: Rostovtsev, VV – volume: 126 start-page: 15046 year: 2004 ident: WOS:000225233600024 article-title: A strain-promoted [3+2] azide-alkyne cycloaddition for covalent modification of blomolecules in living systems publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/ja044996f contributor: fullname: Agard, NJ – volume: 52 start-page: 980 year: 2011 ident: WOS:000287630700008 article-title: One-pot synthesis of 4,5-disubstituted 1,2,3-(NH)-triazoles using terminal acetylenes, carbon monoxide, aryl iodides, and sodium azide publication-title: TETRAHEDRON LETTERS doi: 10.1016/j.tetlet.2010.12.053 contributor: fullname: Li, N – start-page: 3254 year: 2008 ident: WOS:000257552700007 article-title: Conformational control in the regioselective synthesis of N-2-substituted-1,2,3-triazoles publication-title: CHEMICAL COMMUNICATIONS doi: 10.1039/b805328f contributor: fullname: Chen, YF – volume: 8 start-page: 1128 year: 2003 ident: WOS:000187217100009 article-title: The growing impact of click chemistry on drug discovery publication-title: DRUG DISCOVERY TODAY contributor: fullname: Kolb, HC – volume: 106 start-page: 7680 year: 2002 ident: WOS:000177705000006 article-title: Twisted intramolecular charge transfer states in 2-arylbenzotriazoles: Fluorescence deactivation via intramolecular electron transfer rather than proton transfer publication-title: JOURNAL OF PHYSICAL CHEMISTRY A doi: 10.1021/jp021000j contributor: fullname: Maliakal, A – volume: 10 start-page: 5389 year: 2008 ident: WOS:000261294300018 article-title: Efficient Synthesis of N-2-Aryl-1,2,3-Triazole Fluorophores via Post-Triazole Arylation publication-title: ORGANIC LETTERS doi: 10.1021/ol802246q contributor: fullname: Liu, YX – volume: 47 start-page: 10611 year: 2011 ident: WOS:000295004300024 article-title: Synthesis of 2,4,6-trisubstituted pyridines via an olefin cross-metathesis/Heck-cyclisation-elimination sequence publication-title: CHEMICAL COMMUNICATIONS doi: 10.1039/c1cc14257g contributor: fullname: Donohoe, TJ – volume: 10 start-page: 2409 year: 2008 ident: WOS:000256762100021 article-title: Benzyne click chemistry: Synthesis of benzotriazoles from benzynes and azides publication-title: ORGANIC LETTERS doi: 10.1021/ol800675u contributor: fullname: Shi, F – volume: 40 start-page: 7 year: 2007 ident: WOS:000244333400002 article-title: Catalytic azide-alkyne cycloaddition: Reactivity and applications publication-title: ALDRICHIMICA ACTA contributor: fullname: Wu, P – start-page: 1617 year: 2010 ident: WOS:000279048600005 article-title: Metal- and Base-Free Three-Component Reaction of Ynones, Sodium Azide, and Alkyl Halides: Highly Regioselective Synthesis of 2,4,5-Trisubstituted 1,2,3-NH-Triazoles publication-title: SYNLETT doi: 10.1055/s-0030-1258086 contributor: fullname: Li, JH – volume: 8 start-page: 4505 year: 2006 ident: WOS:000240654700031 article-title: Chemoselective formation of successive triazole linkages in one pot: " Click-click" chemistry publication-title: ORGANIC LETTERS doi: 10.1021/ol061657d contributor: fullname: Aucagne, V – volume: 11 start-page: 3024 year: 2009 ident: WOS:000268138800018 article-title: Facile One-Pot Synthesis of 4,5-Disubstituted 1 2,3-(NH)-Triazoles through Sonogashira Coupling/1,3-Dipolar Cycloaddition of Acid Chlorides, Terminal Acetylenes, and Sodium Azide publication-title: ORGANIC LETTERS doi: 10.1021/ol901040d contributor: fullname: Li, JH – volume: 37 start-page: 3370 year: 1972 ident: WOS:A1972N814200048 article-title: H-2-1,2,3-TRIAZOLES FROM ETHYL NITROCINNAMATES publication-title: JOURNAL OF ORGANIC CHEMISTRY contributor: fullname: TANAKA, Y – start-page: 1420 year: 2002 ident: WOS:000176095900003 article-title: The role of the carbonyl group in the intermolecular 1,3-cycloaddition of azido(2-heteroaryl)methanones with activated olefins publication-title: JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 doi: 10.1039/b203577d contributor: fullname: Zanirato, P – volume: 12 start-page: 5414 year: 2010 ident: WOS:000284555600015 article-title: Traceless Azido Linker for the Solid-Phase Synthesis of NH-1,2,3-Triazoles via Cu-Catalyzed Azide-Alkyne Cycloaddition Reactions publication-title: ORGANIC LETTERS doi: 10.1021/ol102209p contributor: fullname: Cohrt, AE – volume: 71 start-page: 8680 year: 2006 ident: WOS:000241435600057 article-title: A study of the scope and regioselectivity of the ruthenium-catalyzed [3+2]-cycloaddition of azides with internal alkynes publication-title: JOURNAL OF ORGANIC CHEMISTRY doi: 10.1021/jo061688m contributor: fullname: Majireck, MM – volume: 59 start-page: 4395 year: 2003 ident: WOS:000183358200018 article-title: Efficient synthesis of 5-fluoroalkylated 1H-1,2,3-triazoles and application of the bromodifluoromethylated triazole to the synthesis of novel bicyclic gem-difluorinated 1H-pyrano[3,4-d] [1,2,3]-triazol-4-one compounds publication-title: TETRAHEDRON doi: 10.1016/S0040-4020(03)00621-5 contributor: fullname: Peng, WM – volume: 131 start-page: 4174 year: 2009 ident: WOS:000264792900002 article-title: Oxidative Palladium Catalysis in SNAr Reactions Leading to Heteroaryl Ethers from Pyridotriazol-1-yloxy Heterocycles with Aryl Boronic Acids publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/ja808622z contributor: fullname: Wacharasindhu, S – volume: 67 start-page: 3057 year: 2002 ident: WOS:000175323600045 article-title: Peptidotriazoles on solid phase: [1,2,3]-triazoles by regiospecific copper(I)-catalyzed 1,3-dipolar cycloadditions of terminal alkynes to azides publication-title: JOURNAL OF ORGANIC CHEMISTRY doi: 10.1021/jo011148j contributor: fullname: Tornoe, CW – volume: 43 start-page: 3928 year: 2004 ident: WOS:000223047200009 article-title: Efficiency and fidelity in a click-chemistry route to triazole dendrimers by the copper(I)-catalyzed ligation of azides and alkynes publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION doi: 10.1002/anie.200454078 contributor: fullname: Wu, P – volume: 2010 start-page: 5409 year: 2010 ident: WOS:000283387900010 article-title: Zn/C-Catalyzed Cycloaddition of Azides and Aryl Alkynes publication-title: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY doi: 10.1002/ejoc.201000610 contributor: fullname: Meng, X – volume: 892 start-page: 210 year: 2008 ident: WOS:000261711400035 article-title: One-pot synthesis and the fluorescent behavior of 4-acetyl-5-methyl-1,2,3-triazole regioisomers publication-title: JOURNAL OF MOLECULAR STRUCTURE doi: 10.1016/j.molstruc.2008.05.028 contributor: fullname: Kamalraj, VR – volume: 48 start-page: 5831 year: 2007 ident: WOS:000248799000025 article-title: Regioselective synthesis of 1,4-disubstituted 1,2,3-triazoles via three-component coupling of secondary alcohols, TMSN3 and alkynes publication-title: TETRAHEDRON LETTERS doi: 10.1016/j.tetlet.2007.06.069 contributor: fullname: Sreedhar, B – volume: 10 start-page: 3171 year: 2008 ident: WOS:000257955100001 article-title: Efficient synthesis of 2-substituted-1,2,3-triazoles publication-title: ORGANIC LETTERS doi: 10.1021/ol8006748 contributor: fullname: Kalisiak, J – volume: 40 start-page: 2004 year: 2001 ident: WOS:000169168100001 article-title: Click chemistry: Diverse chemical function from a few good reactions publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION contributor: fullname: Kolb, HC – volume: 116 start-page: 81 year: 2002 ident: WOS:000177171100016 article-title: 1,3-dipolar cycloaddition of beta-alkoxyvinyl trifluoromethylketones with aryl (or benzyl) azides - Synthesis of 4-trifluoroacetylated 1H-1,2,3-triazoles publication-title: JOURNAL OF FLUORINE CHEMISTRY contributor: fullname: Peng, WM – volume: 125 start-page: 7786 year: 2003 ident: WOS:000183814500018 article-title: Synthesis of triazoles from nonactivated terminal alkynes via the three-component coupling reaction using a Pd(0)-Cu(I) bimetallic catalyst publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/ja034191s contributor: fullname: Kamijo, S – volume: 51 start-page: 1807 year: 1999 ident: WOS:000082079900005 article-title: Synthesis of carbohydrate-derived 1,2,3-triazoles using 1,3-dipolar cycloaddition on a soluble polymer support publication-title: HETEROCYCLES contributor: fullname: Freeze, S – volume: 48 start-page: 161 year: 1998 ident: WOS:000071802800022 article-title: Cycloaddition reactions of azidomethyl phosphonate with acetylenes and enamines. Synthesis of triazoles publication-title: HETEROCYCLES contributor: fullname: Louerat, F – volume: 36 start-page: 2461 year: 2006 ident: WOS:000240162600007 article-title: Simple and efficient one-pot synthesis of 2,4-diaryl-1,2,3-triazoles publication-title: SYNTHETIC COMMUNICATIONS doi: 10.1080/00397910600781216 contributor: fullname: Tang, WJ – volume: 11 start-page: 5026 year: 2009 ident: WOS:000271097100066 article-title: Highly Regioselective N-2 Arylation of 4,5-Dibromo-1,2,3-triazole: Efficient Synthesis of 2-Aryltriazoles publication-title: ORGANIC LETTERS doi: 10.1021/ol9019875 contributor: fullname: Wang, XJ – volume: 13 start-page: 1682 year: 2011 ident: WOS:000288691600027 article-title: A "Click and Activate" Approach in One-Pot Synthesis of a Triazolyl-Pyridazinone Library publication-title: ORGANIC LETTERS doi: 10.1021/ol200183b contributor: fullname: Qian, WY – volume: 44 start-page: 9095 year: 2003 ident: WOS:000298828500008.21 publication-title: TETRAHEDRON LETT contributor: fullname: NORBEDO I – volume: 98 start-page: 4014 year: 1965 ident: WOS:A19657049200027 article-title: 1.3-DIPOLARE CYCLOADDITIONEN .23. EINIGE BEOBACHTUNGEN ZUR ADDITION ORGANISCHER AZIDE AN CC-DREIFACHBINDUNGEN publication-title: CHEMISCHE BERICHTE-RECUEIL contributor: fullname: HUISGEN, R – volume: 71 start-page: 8680 year: 2006 ident: ref3/cit3c publication-title: J. Org. Chem. doi: 10.1021/jo061688m contributor: fullname: Majireck M. M. – volume: 10 start-page: 3171 year: 2008 ident: ref4/cit4c publication-title: Org. Lett. doi: 10.1021/ol8006748 contributor: fullname: Kalisiak J. – volume: 10 start-page: 5389 year: 2008 ident: ref4/cit4d publication-title: Org. Lett. doi: 10.1021/ol802246q contributor: fullname: Liu Y. – volume: 59 start-page: 4395 year: 2003 ident: ref5/cit5a publication-title: Tetrahedron doi: 10.1016/S0040-4020(03)00621-5 contributor: fullname: Peng W. – volume: 37 start-page: 3370 year: 1972 ident: ref6/cit6b publication-title: J. Org. Chem. doi: 10.1021/jo00986a048 contributor: fullname: Tanaka Y. – volume: 41 start-page: 2596 year: 2002 ident: ref1/cit1b publication-title: Angew. Chem., Int. Ed. doi: 10.1002/1521-3773(20020715)41:14<2596::AID-ANIE2596>3.0.CO;2-4 contributor: fullname: Rostovtsev V. V. – volume: 43 start-page: 3928 year: 2004 ident: ref2/cit2c publication-title: Angew. Chem., Int. Ed. doi: 10.1002/anie.200454078 contributor: fullname: Wu P. – volume: 48 start-page: 161 year: 1998 ident: ref5/cit5e publication-title: Heterocycles doi: 10.3987/COM-97-7997 contributor: fullname: Louerat F. – volume: 98 start-page: 4014 year: 1965 ident: ref6/cit6a publication-title: Chem. Ber. doi: 10.1002/cber.19650981228 contributor: fullname: Huisgen R. – volume: 51 start-page: 1807 year: 1999 ident: ref5/cit5d publication-title: Heterocycles doi: 10.3987/COM-99-8518 contributor: fullname: Freeze S. – start-page: 278 year: 2007 ident: ref3/cit3d publication-title: Synlett contributor: fullname: Yang D. – volume: 116 start-page: 81 year: 2002 ident: ref5/cit5b publication-title: J. Fluorine Chem. doi: 10.1016/S0022-1139(02)00103-3 contributor: fullname: Peng W. – start-page: 1617 year: 2010 ident: ref7/cit7b publication-title: Synlett contributor: fullname: Li J – volume: 8 start-page: 1128 year: 2003 ident: ref2/cit2b publication-title: Drug Discovery Today doi: 10.1016/S1359-6446(03)02933-7 contributor: fullname: Kolb H. C. – start-page: 5409 year: 2010 ident: ref7/cit7c publication-title: Eur. J. Org. Chem. doi: 10.1002/ejoc.201000610 contributor: fullname: Meng X. – volume: 106 start-page: 7680 year: 2002 ident: ref2/cit2a publication-title: J. Phys. Chem. A doi: 10.1021/jp021000j contributor: fullname: Maliakal A. – start-page: 3254 year: 2008 ident: ref4/cit4b publication-title: Chem. Commun. doi: 10.1039/b805328f contributor: fullname: Chen Y. – volume: 13 start-page: 1682 year: 2011 ident: ref3/cit3g publication-title: Org. Lett. doi: 10.1021/ol200183b contributor: fullname: Qian W. – volume: 8 start-page: 4505 year: 2006 ident: ref3/cit3b publication-title: Org. Lett. doi: 10.1021/ol061657d contributor: fullname: Aucagne V. – volume: 40 start-page: 2004 year: 2001 ident: ref1/cit1a publication-title: Angew. Chem., Int.Ed. doi: 10.1002/1521-3773(20010601)40:11<2004::AID-ANIE2004>3.0.CO;2-5 contributor: fullname: Kolb H. C. – start-page: 10611 year: 2011 ident: ref6/cit6e publication-title: Chem. Commun. doi: 10.1039/c1cc14257g contributor: fullname: Donohoe T. J. – volume: 131 start-page: 4174 year: 2009 ident: ref2/cit2f publication-title: J. Am. Chem. Soc. doi: 10.1021/ja808622z contributor: fullname: Wacharasindhu S. – volume: 892 start-page: 210 year: 2008 ident: ref6/cit6d publication-title: J. Mol. Struct. doi: 10.1016/j.molstruc.2008.05.028 contributor: fullname: Kamalraj V. R. – volume: 40 start-page: 7 year: 2007 ident: ref1/cit1c publication-title: Aldrichimica Acta contributor: fullname: Wu P. – volume: 11 start-page: 5026 year: 2009 ident: ref4/cit4e publication-title: Org. Lett. doi: 10.1021/ol9019875 contributor: fullname: Wang X. – volume: 44 start-page: 9095 year: 2003 ident: ref6/cit6c publication-title: Tetrahedron Lett. doi: 10.1016/j.tetlet.2003.10.051 contributor: fullname: Norbedo I. – volume: 12 start-page: 5414 year: 2011 ident: ref1/cit1d publication-title: Org. Lett. doi: 10.1021/ol102209p contributor: fullname: Cohrt A. E. – volume: 36 start-page: 2461 year: 2006 ident: ref8/cit8 publication-title: Synth. Commun. doi: 10.1080/00397910600781216 contributor: fullname: Tang W. – volume: 52 start-page: 980 year: 2011 ident: ref7/cit7d publication-title: Tetrahedron Lett. doi: 10.1016/j.tetlet.2010.12.053 contributor: fullname: Li N. – volume: 10 start-page: 2409 year: 2008 ident: ref3/cit3f publication-title: Org. Lett. doi: 10.1021/ol800675u contributor: fullname: Shi F. – volume: 125 start-page: 7786 year: 2002 ident: ref4/cit4a publication-title: J. Am. Chem. Soc. doi: 10.1021/ja034191s contributor: fullname: Kamijo S. – volume: 48 start-page: 5831 year: 2007 ident: ref3/cit3e publication-title: Tetrahedron Lett. doi: 10.1016/j.tetlet.2007.06.069 contributor: fullname: Sreedhar B. – volume: 126 start-page: 15046 year: 2004 ident: ref2/cit2d publication-title: J. Am. Chem. Soc. doi: 10.1021/ja044996f contributor: fullname: Agard N. J. – start-page: 1420 year: 2002 ident: ref5/cit5c publication-title: J. Chem. Soc., Perkin Trans. 1 doi: 10.1039/b203577d contributor: fullname: Zanirato P. – volume: 11 start-page: 3024 year: 2009 ident: ref7/cit7a publication-title: Org. Lett. doi: 10.1021/ol901040d contributor: fullname: Li J. – volume: 67 start-page: 3057 year: 2002 ident: ref3/cit3a publication-title: J. Org. Chem. doi: 10.1021/jo011148j contributor: fullname: Tornøe C. W. |
| SSID | ssj0011529 |
| Score | 2.4139984 |
| Snippet | An efficient one-pot three-component stepwise approach for the synthesis of N-2-aryl-substituted-1,2,3-triazoles has been developed. By using this... |
| Source | Web of Science |
| SourceID | proquest crossref pubmed webofscience acs |
| SourceType | Aggregation Database Index Database Enrichment Source Publisher |
| StartPage | 26 |
| SubjectTerms | Chemistry Chemistry, Organic Physical Sciences Science & Technology |
| Title | CuO-Promoted Construction of N-2-Aryl-Substituted-1,2,3-Triazoles via Azide-Chalcone Oxidative Cycloaddition and Post-Triazole Arylation |
| URI | http://dx.doi.org/10.1021/ol202718d http://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcApp=Summon&SrcAuth=ProQuest&DestApp=WOS&DestLinkType=FullRecord&UT=000298828500008 https://www.ncbi.nlm.nih.gov/pubmed/22133007 https://search.proquest.com/docview/914673235 |
| Volume | 14 |
| WOS | 000298828500008 |
| WOSCitedRecordID | wos000298828500008 |
| hasFullText | 1 |
| inHoldings | 1 |
| isFullTextHit | |
| isPrint | |
| link | http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwjV3dT9swED8x9rC9MPZJNoaswSNmsZ26yWOVDaFJg0mAxFvk2hetWtVOtEXQv4A_e3dOEzHBPl6iKLEt23fO_Zw7_w5gDz0Gi0pJG7JMZt5aWTiDsq9zPikavIrugq_H9ug8-3LRu1iD3T948LX6OB3z_lzl4RE81hw5yPinPO1cBWSAikiKqo1kKpiWPuhuVTY9fva76bmHJx80PdHMHD6DT-1hnSa65MfBYj488Mv73I1_G8EmbKxgphg0evEc1nDyAp6UbXa3l3BbLk7ktxiLh0Fw2s6WSFZMa3EstRxc3owlf1eaYIIg1b7eN_KMNHbJLFDiauTEYDkKKMvvjv1aKE6uRyEyiYvyxo-nHKwUm3STIDgtcFdbcOtRKV7B6eHns_JIrrIySGfydC4dIQrrVE0bDYVpUQdNyNcH37OmDipFkoPP-nmdYo30wBiX0RXROJP52ryG9Ql1aAuELnzaqzXtz4cm6w91gY7urHKFzwmHYgI7JLRqtaZmVXSXa1V105nAh1ae1c-Gm-OhQqKVdEVTzO4QN8HpYlYVbCSMNr0E3jQa0LWiNfWb0FMCe3dVonufRuZ6Jv-LmDsB9T_FyhXrOrMNzN_-a3Tv4CmBMx1_99htWCctwPcEgObDnbgAfgHGvP4X |
| link.rule.ids | 315,786,790,2782,27109,27957,27958,57093,57143 |
| linkProvider | American Chemical Society |
| linkToHtml | http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwjV1Lb9QwEB5BOZQLb2gKFAv1WJfYTrzJcRVRLdBukbpIvUVeeyJWXe0isova_QX8bMbOgwKV6CWKEnvkxzjzOTP-BmAfLTqNQnDtkoQnVmueG4V8IDN_UtRZEdwFJ2M9-pJ8PE_PW5ocfxaGGlGTpDo48X-zC4h3y7nfpovM3YV76YD24R4GFWe9x4DsUB64UaXinhGmYxG6XtVbIFv_aYH-gZU3WqBgbY4eNmmLQjtDkMnF4Xo1PbSbvygcb9eRR_CgBZ1s2GjJY7iDiyewXXS53p7Cz2J9yj-HyDx0zCfx7Ghl2bJiYy758PvVnPuvTBNa4Lg4kAeKT0h_N54Tiv2YGTbczBzy4qvxXi5kp5czF3jFWXFl50sfuhREmoVjPklwX5t56UFFnsHZ0ftJMeJtjgZuVBavuCF8oY2oaNshMM4rJwkHW2dTrSonYqTpsMkgq2KskB4oZRK6IiqjElup57C1oAbtAJO5jdNK0m59qpLBVOZo6E4Lk9uMUClGsEejWbYrrC6D81yKsh_OCN5201p-a5g6birEugkvaYi9c8QscLmuy9ybDCVVGsGLRhF6KVJSuwlLRbB_XTP693HgsfdUgAGBRyBuU6xoOdg998Bq93-9ewPbo8nJcXn8YfzpJdwn2CbDjyD9CrZII_A1QaPVdC-siV_LqgaR |
| linkToPdf | http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwjV1Zb9QwEB5BkYAX7iMcxUJ9rEtsJ97kcRVYlWu3UovUt8jrQ6xY7VZkF9H9BfxsZrxJVKASfYmixB75GGc-Z8bfAOx56532QnDtsoxnVmteGuX5QBZ0UtRZEd0Fn8f68Ev24TQ_bTeKdBYGG9GgpCY68WlVn7nQMgyIN8s5bdVF4a7DjZwSdxMUqo57rwHaojLyo0rFiRWmYxK6WJWskG3-tEL_QMtLrVC0OKO7MOnbGgNNvh2sV9MDu_mLxvHqnbkHd1rwyYZbbbkP1_ziAdyqupxvD-FXtZ7woxih5x2jZJ4dvSxbBjbmkg-_n885fW22IQaOi325r_gJ6vGGuKHYj5lhw83MeV59NeTt8mzyc-Yivzirzu18SSFMUaRZOEbJgvvajKRHVXkEx6N3J9Uhb3M1cKOKdMUN4gxtRMDth_BpGZxEPGydzbUKTqQep8RmgyKkPnh8oJTJ8Oq9MiqzQT2GnQU26CkwWdo0DxJ37VOVDaay9AbvtDClLRCd-gR2cUTrdqU1dXSiS1H3w5nA625q67MtY8dlhVg36TUOMTlJzMIv101dkulQUuUJPNkqQy9FSmw3YqoE9i5qR_8-jXz2RAkYkXgC4irFqpaLnTgIVs_-17tXcPPo7aj-9H788TncRvQm4_8g_QJ2UCH8S0RIq-luXBa_AT-FCQs |
| 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=CuO-Promoted+Construction+of+N-2-Aryl-Substituted-1%2C2%2C3-Triazoles+via+Azide-Chalcone+Oxidative+Cycloaddition+and+Post-Triazole+Arylation&rft.jtitle=Organic+letters&rft.au=Zhang%2C+Yuanqing&rft.au=Li%2C+Xiaolong&rft.au=Li%2C+Jihui&rft.au=Chen%2C+Jinying&rft.date=2012-01-06&rft.pub=Amer+Chemical+Soc&rft.issn=1523-7060&rft.eissn=1523-7052&rft.volume=14&rft.issue=1&rft.spage=26&rft.epage=29&rft_id=info:doi/10.1021%2Fol202718d&rft_id=info%3Apmid%2F22133007&rft.externalDBID=n%2Fa&rft.externalDocID=000298828500008 |
| thumbnail_l | http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/lc.gif&issn=1523-7060&client=summon |
| thumbnail_m | http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/mc.gif&issn=1523-7060&client=summon |
| thumbnail_s | http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/sc.gif&issn=1523-7060&client=summon |