Electro-Oxidative C-N Bond Formation through Azolation of Indole Derivatives: An Access to 3-Substituent-2-(Azol-1-yl)indoles

Electro-Oxidative C-N Bond Formation through Azolation of Indole Derivatives: An Access to 3-Substituent-2-(Azol-1-yl)indoles

A practical protocol to synthesize 3-substituent-2-(azol-1-yl)indole derivatives has been developed via an electrochemical oxidative cross coupling process under mild conditions. This electro-oxidative C-N bond formation strategy tolerates a range of functional groups and is amenable to gram scale s...

Ausführliche Beschreibung

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:Journal of organic chemistry 2021-11, Vol.86 (22), p.16059-16067
Hauptverfasser: Zhou, Naifu, Zhao, Junhao, Sun, Chengbo, Lai, Yuqin, Ruan, Zhixiong, Feng, Pengju
Format: Artikel
Sprache:eng
Schlagworte:
Danazol
Indoles
Molecular Structure
Oxidative Stress
Online-Zugang:Volltext
Tags: Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
container_end_page 16067
container_issue 22
container_start_page 16059
container_title Journal of organic chemistry
container_volume 86
creator Zhou, Naifu
Zhao, Junhao
Sun, Chengbo
Lai, Yuqin
Ruan, Zhixiong
Feng, Pengju
description A practical protocol to synthesize 3-substituent-2-(azol-1-yl)indole derivatives has been developed via an electrochemical oxidative cross coupling process under mild conditions. This electro-oxidative C-N bond formation strategy tolerates a range of functional groups and is amenable to gram scale synthesis. Moreover, this method was applied to the late-stage functionalization of bioactive molecules.
doi_str_mv 10.1021/acs.joc.1c01271
format Article
fullrecord <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_2572935196</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>2572935196</sourcerecordid><originalsourceid>FETCH-LOGICAL-c297t-c22d7b9e2482765449efb0a215ddeddbb7c2f21ff70ef19ff09cbb88fdb8dde73</originalsourceid><addsrcrecordid>eNo9kEtPAjEURhujEUTX7kyXuCi0nWfdIYKaEFmo68n0JUOGKbYdIib-d8tD7-Le5Mv57uIAcE3wgGBKhqVwg6URAyIwoRk5AV2SUIxShuNT0MWYUhTRNOqAC-eWOEySJOegE8WBIox0wc-kVsJbg-ZflSx9tVFwjF7gvWkknBq7CpFpoF9Y034s4Ojb1IfEaPjcSFMr-KBstdk33R0cNXAkhHIOegMj9Npy5yvfqsYjivq7OiJoW99W-667BGe6rJ26Ot4eeJ9O3sZPaDZ_fB6PZkhQlvmwqcw4UzTOaZYmccyU5rikJJFSScl5JqimROsMK02Y1pgJzvNcS54HIot6oH_4u7bms1XOF6vKCVXXZaNM6wqaZJRFCWFpQIcHVFjjnFW6WNtqVdptQXCxc14E50VwXhydh8bN8XnLV0r-83-So191-H-j</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>2572935196</pqid></control><display><type>article</type><title>Electro-Oxidative C-N Bond Formation through Azolation of Indole Derivatives: An Access to 3-Substituent-2-(Azol-1-yl)indoles</title><source>MEDLINE</source><source>American Chemical Society Journals</source><creator>Zhou, Naifu ; Zhao, Junhao ; Sun, Chengbo ; Lai, Yuqin ; Ruan, Zhixiong ; Feng, Pengju</creator><creatorcontrib>Zhou, Naifu ; Zhao, Junhao ; Sun, Chengbo ; Lai, Yuqin ; Ruan, Zhixiong ; Feng, Pengju</creatorcontrib><description>A practical protocol to synthesize 3-substituent-2-(azol-1-yl)indole derivatives has been developed via an electrochemical oxidative cross coupling process under mild conditions. This electro-oxidative C-N bond formation strategy tolerates a range of functional groups and is amenable to gram scale synthesis. Moreover, this method was applied to the late-stage functionalization of bioactive molecules.</description><identifier>ISSN: 0022-3263</identifier><identifier>EISSN: 1520-6904</identifier><identifier>DOI: 10.1021/acs.joc.1c01271</identifier><identifier>PMID: 34520191</identifier><language>eng</language><publisher>United States</publisher><subject>Danazol ; Indoles ; Molecular Structure ; Oxidative Stress</subject><ispartof>Journal of organic chemistry, 2021-11, Vol.86 (22), p.16059-16067</ispartof><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c297t-c22d7b9e2482765449efb0a215ddeddbb7c2f21ff70ef19ff09cbb88fdb8dde73</citedby><cites>FETCH-LOGICAL-c297t-c22d7b9e2482765449efb0a215ddeddbb7c2f21ff70ef19ff09cbb88fdb8dde73</cites><orcidid>0000-0002-5470-0403</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,2763,27923,27924</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/34520191$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Zhou, Naifu</creatorcontrib><creatorcontrib>Zhao, Junhao</creatorcontrib><creatorcontrib>Sun, Chengbo</creatorcontrib><creatorcontrib>Lai, Yuqin</creatorcontrib><creatorcontrib>Ruan, Zhixiong</creatorcontrib><creatorcontrib>Feng, Pengju</creatorcontrib><title>Electro-Oxidative C-N Bond Formation through Azolation of Indole Derivatives: An Access to 3-Substituent-2-(Azol-1-yl)indoles</title><title>Journal of organic chemistry</title><addtitle>J Org Chem</addtitle><description>A practical protocol to synthesize 3-substituent-2-(azol-1-yl)indole derivatives has been developed via an electrochemical oxidative cross coupling process under mild conditions. This electro-oxidative C-N bond formation strategy tolerates a range of functional groups and is amenable to gram scale synthesis. Moreover, this method was applied to the late-stage functionalization of bioactive molecules.</description><subject>Danazol</subject><subject>Indoles</subject><subject>Molecular Structure</subject><subject>Oxidative Stress</subject><issn>0022-3263</issn><issn>1520-6904</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2021</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNo9kEtPAjEURhujEUTX7kyXuCi0nWfdIYKaEFmo68n0JUOGKbYdIib-d8tD7-Le5Mv57uIAcE3wgGBKhqVwg6URAyIwoRk5AV2SUIxShuNT0MWYUhTRNOqAC-eWOEySJOegE8WBIox0wc-kVsJbg-ZflSx9tVFwjF7gvWkknBq7CpFpoF9Y034s4Ojb1IfEaPjcSFMr-KBstdk33R0cNXAkhHIOegMj9Npy5yvfqsYjivq7OiJoW99W-667BGe6rJ26Ot4eeJ9O3sZPaDZ_fB6PZkhQlvmwqcw4UzTOaZYmccyU5rikJJFSScl5JqimROsMK02Y1pgJzvNcS54HIot6oH_4u7bms1XOF6vKCVXXZaNM6wqaZJRFCWFpQIcHVFjjnFW6WNtqVdptQXCxc14E50VwXhydh8bN8XnLV0r-83-So191-H-j</recordid><startdate>20211119</startdate><enddate>20211119</enddate><creator>Zhou, Naifu</creator><creator>Zhao, Junhao</creator><creator>Sun, Chengbo</creator><creator>Lai, Yuqin</creator><creator>Ruan, Zhixiong</creator><creator>Feng, Pengju</creator><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0002-5470-0403</orcidid></search><sort><creationdate>20211119</creationdate><title>Electro-Oxidative C-N Bond Formation through Azolation of Indole Derivatives: An Access to 3-Substituent-2-(Azol-1-yl)indoles</title><author>Zhou, Naifu ; Zhao, Junhao ; Sun, Chengbo ; Lai, Yuqin ; Ruan, Zhixiong ; Feng, Pengju</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c297t-c22d7b9e2482765449efb0a215ddeddbb7c2f21ff70ef19ff09cbb88fdb8dde73</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2021</creationdate><topic>Danazol</topic><topic>Indoles</topic><topic>Molecular Structure</topic><topic>Oxidative Stress</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Zhou, Naifu</creatorcontrib><creatorcontrib>Zhao, Junhao</creatorcontrib><creatorcontrib>Sun, Chengbo</creatorcontrib><creatorcontrib>Lai, Yuqin</creatorcontrib><creatorcontrib>Ruan, Zhixiong</creatorcontrib><creatorcontrib>Feng, Pengju</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Zhou, Naifu</au><au>Zhao, Junhao</au><au>Sun, Chengbo</au><au>Lai, Yuqin</au><au>Ruan, Zhixiong</au><au>Feng, Pengju</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Electro-Oxidative C-N Bond Formation through Azolation of Indole Derivatives: An Access to 3-Substituent-2-(Azol-1-yl)indoles</atitle><jtitle>Journal of organic chemistry</jtitle><addtitle>J Org Chem</addtitle><date>2021-11-19</date><risdate>2021</risdate><volume>86</volume><issue>22</issue><spage>16059</spage><epage>16067</epage><pages>16059-16067</pages><issn>0022-3263</issn><eissn>1520-6904</eissn><abstract>A practical protocol to synthesize 3-substituent-2-(azol-1-yl)indole derivatives has been developed via an electrochemical oxidative cross coupling process under mild conditions. This electro-oxidative C-N bond formation strategy tolerates a range of functional groups and is amenable to gram scale synthesis. Moreover, this method was applied to the late-stage functionalization of bioactive molecules.</abstract><cop>United States</cop><pmid>34520191</pmid><doi>10.1021/acs.joc.1c01271</doi><tpages>9</tpages><orcidid>https://orcid.org/0000-0002-5470-0403</orcidid></addata></record>
fulltext fulltext
identifier ISSN: 0022-3263
ispartof Journal of organic chemistry, 2021-11, Vol.86 (22), p.16059-16067
issn 0022-3263
1520-6904
language eng
recordid cdi_proquest_miscellaneous_2572935196
source MEDLINE; American Chemical Society Journals
subjects Danazol
Indoles
Molecular Structure
Oxidative Stress
title Electro-Oxidative C-N Bond Formation through Azolation of Indole Derivatives: An Access to 3-Substituent-2-(Azol-1-yl)indoles
url https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-10T10%3A20%3A47IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_cross&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Electro-Oxidative%20C-N%20Bond%20Formation%20through%20Azolation%20of%20Indole%20Derivatives:%20An%20Access%20to%203-Substituent-2-(Azol-1-yl)indoles&rft.jtitle=Journal%20of%20organic%20chemistry&rft.au=Zhou,%20Naifu&rft.date=2021-11-19&rft.volume=86&rft.issue=22&rft.spage=16059&rft.epage=16067&rft.pages=16059-16067&rft.issn=0022-3263&rft.eissn=1520-6904&rft_id=info:doi/10.1021/acs.joc.1c01271&rft_dat=%3Cproquest_cross%3E2572935196%3C/proquest_cross%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_pqid=2572935196&rft_id=info:pmid/34520191&rfr_iscdi=true