Synthesis of Multisubstituted 1,2,3-Triazoles: Regioselective Formation and Reaction Mechanism

Synthesis of Multisubstituted 1,2,3-Triazoles: Regioselective Formation and Reaction Mechanism

A synthetically useful approach to functionalized triazoles is described via the reaction of β-carbonyl phosphonates and azides. 1,4- and 1,5-disubstituted and 1,4,5-trisubstituted triazoles can be regio- and chemoselectively accessed under mild conditions in good to excellent yields (31 examples, u...

Ausführliche Beschreibung

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:Journal of organic chemistry 2024-04, Vol.89 (8), p.5401-5408
Hauptverfasser: Chi, Tzu-Ching, Yang, Po-Chun, Hung, Shao-Kung, Wu, Hui-Wen, Wang, Hong-Chi, Liu, Hsin-Kuan, Liu, Li-Wen, Chou, Ho-Hsuan
Format: Artikel
Sprache:eng
Online-Zugang:Volltext
Tags: Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
container_end_page 5408
container_issue 8
container_start_page 5401
container_title Journal of organic chemistry
container_volume 89
creator Chi, Tzu-Ching
Yang, Po-Chun
Hung, Shao-Kung
Wu, Hui-Wen
Wang, Hong-Chi
Liu, Hsin-Kuan
Liu, Li-Wen
Chou, Ho-Hsuan
description A synthetically useful approach to functionalized triazoles is described via the reaction of β-carbonyl phosphonates and azides. 1,4- and 1,5-disubstituted and 1,4,5-trisubstituted triazoles can be regio- and chemoselectively accessed under mild conditions in good to excellent yields (31 examples, up to 99%). A mechanism is proposed that rationalizes the avoidance of the 4-phosphonate byproducts, which is aligned with crystallographic and experimental evidence.
doi_str_mv 10.1021/acs.joc.3c02836
format Article
fullrecord <record><control><sourceid>proquest_pubme</sourceid><recordid>TN_cdi_pubmedcentral_primary_oai_pubmedcentral_nih_gov_11040735</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>3014010317</sourcerecordid><originalsourceid>FETCH-LOGICAL-a384t-9561d78a89a373e6784f363d533e37bcae36abd97cc744eca549188ce25021d23</originalsourceid><addsrcrecordid>eNp1kc9LHTEQx0Npqa_ac29ljwXdZ5JJ9kcvRURrQRH8cW2Yl53ni-xubJIV9K9v7HtKPZhLCPOZ74T5MPZF8LngUuyjjfNbb-dguWygesdmQkteVi1X79mMcylLkBVssU8x3vJ8tNYf2RY0WlUa2hn7ffkwphVFFwu_LM6mPrk4LWJyaUrUFWJP7kF5FRw--p7i9-KCbpyP1JNN7p6KYx8GTM6PBY5dLqL99zgju8LRxWGHfVhiH-nz5t5m18dHV4cn5en5z1-HB6clQqNS2epKdHWDTYtQA1V1o5ZQQacBCOqFRYIKF11bW1srRRa1akXTWJI6b6GTsM1-rHPvpsVAnaUxBezNXXADhgfj0ZnXldGtzI2_N0JwxWvQOeHbJiH4PxPFZAYXLfU9juSnaIALxQUHUWd0f43a4GMMtHyZI7h50mKyFpO1mI2W3PH1_--98M8eMrC7BtadUxjztt6M-wswCJmv</addsrcrecordid><sourcetype>Open Access Repository</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>3014010317</pqid></control><display><type>article</type><title>Synthesis of Multisubstituted 1,2,3-Triazoles: Regioselective Formation and Reaction Mechanism</title><source>American Chemical Society Journals</source><creator>Chi, Tzu-Ching ; Yang, Po-Chun ; Hung, Shao-Kung ; Wu, Hui-Wen ; Wang, Hong-Chi ; Liu, Hsin-Kuan ; Liu, Li-Wen ; Chou, Ho-Hsuan</creator><creatorcontrib>Chi, Tzu-Ching ; Yang, Po-Chun ; Hung, Shao-Kung ; Wu, Hui-Wen ; Wang, Hong-Chi ; Liu, Hsin-Kuan ; Liu, Li-Wen ; Chou, Ho-Hsuan</creatorcontrib><description>A synthetically useful approach to functionalized triazoles is described via the reaction of β-carbonyl phosphonates and azides. 1,4- and 1,5-disubstituted and 1,4,5-trisubstituted triazoles can be regio- and chemoselectively accessed under mild conditions in good to excellent yields (31 examples, up to 99%). A mechanism is proposed that rationalizes the avoidance of the 4-phosphonate byproducts, which is aligned with crystallographic and experimental evidence.</description><identifier>ISSN: 0022-3263</identifier><identifier>EISSN: 1520-6904</identifier><identifier>DOI: 10.1021/acs.joc.3c02836</identifier><identifier>PMID: 38546539</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><ispartof>Journal of organic chemistry, 2024-04, Vol.89 (8), p.5401-5408</ispartof><rights>2024 The Authors. Published by American Chemical Society</rights><rights>2024 The Authors. Published by American Chemical Society 2024 The Authors</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><cites>FETCH-LOGICAL-a384t-9561d78a89a373e6784f363d533e37bcae36abd97cc744eca549188ce25021d23</cites><orcidid>0000-0002-8183-3922</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/acs.joc.3c02836$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/acs.joc.3c02836$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>230,314,780,784,885,2765,27076,27924,27925,56738,56788</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/38546539$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Chi, Tzu-Ching</creatorcontrib><creatorcontrib>Yang, Po-Chun</creatorcontrib><creatorcontrib>Hung, Shao-Kung</creatorcontrib><creatorcontrib>Wu, Hui-Wen</creatorcontrib><creatorcontrib>Wang, Hong-Chi</creatorcontrib><creatorcontrib>Liu, Hsin-Kuan</creatorcontrib><creatorcontrib>Liu, Li-Wen</creatorcontrib><creatorcontrib>Chou, Ho-Hsuan</creatorcontrib><title>Synthesis of Multisubstituted 1,2,3-Triazoles: Regioselective Formation and Reaction Mechanism</title><title>Journal of organic chemistry</title><addtitle>J. Org. Chem</addtitle><description>A synthetically useful approach to functionalized triazoles is described via the reaction of β-carbonyl phosphonates and azides. 1,4- and 1,5-disubstituted and 1,4,5-trisubstituted triazoles can be regio- and chemoselectively accessed under mild conditions in good to excellent yields (31 examples, up to 99%). A mechanism is proposed that rationalizes the avoidance of the 4-phosphonate byproducts, which is aligned with crystallographic and experimental evidence.</description><issn>0022-3263</issn><issn>1520-6904</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2024</creationdate><recordtype>article</recordtype><recordid>eNp1kc9LHTEQx0Npqa_ac29ljwXdZ5JJ9kcvRURrQRH8cW2Yl53ni-xubJIV9K9v7HtKPZhLCPOZ74T5MPZF8LngUuyjjfNbb-dguWygesdmQkteVi1X79mMcylLkBVssU8x3vJ8tNYf2RY0WlUa2hn7ffkwphVFFwu_LM6mPrk4LWJyaUrUFWJP7kF5FRw--p7i9-KCbpyP1JNN7p6KYx8GTM6PBY5dLqL99zgju8LRxWGHfVhiH-nz5t5m18dHV4cn5en5z1-HB6clQqNS2epKdHWDTYtQA1V1o5ZQQacBCOqFRYIKF11bW1srRRa1akXTWJI6b6GTsM1-rHPvpsVAnaUxBezNXXADhgfj0ZnXldGtzI2_N0JwxWvQOeHbJiH4PxPFZAYXLfU9juSnaIALxQUHUWd0f43a4GMMtHyZI7h50mKyFpO1mI2W3PH1_--98M8eMrC7BtadUxjztt6M-wswCJmv</recordid><startdate>20240419</startdate><enddate>20240419</enddate><creator>Chi, Tzu-Ching</creator><creator>Yang, Po-Chun</creator><creator>Hung, Shao-Kung</creator><creator>Wu, Hui-Wen</creator><creator>Wang, Hong-Chi</creator><creator>Liu, Hsin-Kuan</creator><creator>Liu, Li-Wen</creator><creator>Chou, Ho-Hsuan</creator><general>American Chemical Society</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope><scope>5PM</scope><orcidid>https://orcid.org/0000-0002-8183-3922</orcidid></search><sort><creationdate>20240419</creationdate><title>Synthesis of Multisubstituted 1,2,3-Triazoles: Regioselective Formation and Reaction Mechanism</title><author>Chi, Tzu-Ching ; Yang, Po-Chun ; Hung, Shao-Kung ; Wu, Hui-Wen ; Wang, Hong-Chi ; Liu, Hsin-Kuan ; Liu, Li-Wen ; Chou, Ho-Hsuan</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a384t-9561d78a89a373e6784f363d533e37bcae36abd97cc744eca549188ce25021d23</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2024</creationdate><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Chi, Tzu-Ching</creatorcontrib><creatorcontrib>Yang, Po-Chun</creatorcontrib><creatorcontrib>Hung, Shao-Kung</creatorcontrib><creatorcontrib>Wu, Hui-Wen</creatorcontrib><creatorcontrib>Wang, Hong-Chi</creatorcontrib><creatorcontrib>Liu, Hsin-Kuan</creatorcontrib><creatorcontrib>Liu, Li-Wen</creatorcontrib><creatorcontrib>Chou, Ho-Hsuan</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><collection>PubMed Central (Full Participant titles)</collection><jtitle>Journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Chi, Tzu-Ching</au><au>Yang, Po-Chun</au><au>Hung, Shao-Kung</au><au>Wu, Hui-Wen</au><au>Wang, Hong-Chi</au><au>Liu, Hsin-Kuan</au><au>Liu, Li-Wen</au><au>Chou, Ho-Hsuan</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis of Multisubstituted 1,2,3-Triazoles: Regioselective Formation and Reaction Mechanism</atitle><jtitle>Journal of organic chemistry</jtitle><addtitle>J. Org. Chem</addtitle><date>2024-04-19</date><risdate>2024</risdate><volume>89</volume><issue>8</issue><spage>5401</spage><epage>5408</epage><pages>5401-5408</pages><issn>0022-3263</issn><eissn>1520-6904</eissn><abstract>A synthetically useful approach to functionalized triazoles is described via the reaction of β-carbonyl phosphonates and azides. 1,4- and 1,5-disubstituted and 1,4,5-trisubstituted triazoles can be regio- and chemoselectively accessed under mild conditions in good to excellent yields (31 examples, up to 99%). A mechanism is proposed that rationalizes the avoidance of the 4-phosphonate byproducts, which is aligned with crystallographic and experimental evidence.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>38546539</pmid><doi>10.1021/acs.joc.3c02836</doi><tpages>8</tpages><orcidid>https://orcid.org/0000-0002-8183-3922</orcidid><oa>free_for_read</oa></addata></record>
fulltext fulltext
identifier ISSN: 0022-3263
ispartof Journal of organic chemistry, 2024-04, Vol.89 (8), p.5401-5408
issn 0022-3263
1520-6904
language eng
recordid cdi_pubmedcentral_primary_oai_pubmedcentral_nih_gov_11040735
source American Chemical Society Journals
title Synthesis of Multisubstituted 1,2,3-Triazoles: Regioselective Formation and Reaction Mechanism
url https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2024-12-27T08%3A05%3A59IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_pubme&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Synthesis%20of%20Multisubstituted%201,2,3-Triazoles:%20Regioselective%20Formation%20and%20Reaction%20Mechanism&rft.jtitle=Journal%20of%20organic%20chemistry&rft.au=Chi,%20Tzu-Ching&rft.date=2024-04-19&rft.volume=89&rft.issue=8&rft.spage=5401&rft.epage=5408&rft.pages=5401-5408&rft.issn=0022-3263&rft.eissn=1520-6904&rft_id=info:doi/10.1021/acs.joc.3c02836&rft_dat=%3Cproquest_pubme%3E3014010317%3C/proquest_pubme%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_pqid=3014010317&rft_id=info:pmid/38546539&rfr_iscdi=true