Oxidative radical cascade cyclization involving C(sp 3 )–C(sp 3 ), C(sp 3 )–C(sp 2 ) and C(sp 2 )–N bonds formation: direct construction of cyano and methyl substituted polyheterocycles

An oxidative radical cascade cyclization of 2-cyano-3-arylaniline derived acrylamides with acetonitrile has been developed. The reaction provides a straightforward and practical access to cyano substituted pyrido[4,3,2- gh ]phenanthridines, and exhibits a good functional group tolerance. Furthermore...

Ausführliche Beschreibung

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:Organic Chemistry Frontiers 2018-06, Vol.5 (12), p.1945-1949
Hauptverfasser: Shang, Jia-Qi, Wang, Shi-Sheng, Fu, Hong, Li, Yi, Yang, Tao, Li, Ya-Min
Format: Artikel
Sprache:eng
Schlagworte:
Online-Zugang:Volltext
Tags: Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
container_end_page 1949
container_issue 12
container_start_page 1945
container_title Organic Chemistry Frontiers
container_volume 5
creator Shang, Jia-Qi
Wang, Shi-Sheng
Fu, Hong
Li, Yi
Yang, Tao
Li, Ya-Min
description An oxidative radical cascade cyclization of 2-cyano-3-arylaniline derived acrylamides with acetonitrile has been developed. The reaction provides a straightforward and practical access to cyano substituted pyrido[4,3,2- gh ]phenanthridines, and exhibits a good functional group tolerance. Furthermore, such methyl substituted polyheterocycles were also obtained through a similar radical cascade.
doi_str_mv 10.1039/C8QO00336J
format Article
fullrecord <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_journals_2053509746</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>2053509746</sourcerecordid><originalsourceid>FETCH-LOGICAL-c259t-9edd28a688bea68d9aaedc20baadee009dccc2f454728034cfd56af6f576be983</originalsourceid><addsrcrecordid>eNplUUtOwzAQjRBIVNANJxiJDUUEHCdOYnYo4quKCgnWkWM71FUaB9upCCvuwIG4CychbalAYjP_mTczz_MOAnQaoJCeZenDBKEwjO-2vAFGBPtRgOn2H3vXG1o7QwgFmMSIJAPvc_KqBHNqIcEwoTirgDPLmZDAO16ptz6na1D1QlcLVT9DdmQbCGH09f6xMU_-BTGMgNUCNk4fv4dC18JCqc18NfMchDKSO-C6ts60fAWkyx6X1XrVPpdu2lVg28I65VonBTS66qbSSaOX60m77-2UrLJy-KP3vKery8fsxh9Prm-zi7HPMaHOp1IInLI4TQvZS0EZk4JjVLD-UokQFZxzXEYkSnCKwoiXgsSsjEuSxIWkabjnHa7nNka_tNK6fKZbU_eQef_dkCCaRHFfdbyu4kZba2SZN0bNmenyAOVLjvJfjsJvPpCHXA</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>2053509746</pqid></control><display><type>article</type><title>Oxidative radical cascade cyclization involving C(sp 3 )–C(sp 3 ), C(sp 3 )–C(sp 2 ) and C(sp 2 )–N bonds formation: direct construction of cyano and methyl substituted polyheterocycles</title><source>Royal Society Of Chemistry Journals 2008-</source><creator>Shang, Jia-Qi ; Wang, Shi-Sheng ; Fu, Hong ; Li, Yi ; Yang, Tao ; Li, Ya-Min</creator><creatorcontrib>Shang, Jia-Qi ; Wang, Shi-Sheng ; Fu, Hong ; Li, Yi ; Yang, Tao ; Li, Ya-Min</creatorcontrib><description>An oxidative radical cascade cyclization of 2-cyano-3-arylaniline derived acrylamides with acetonitrile has been developed. The reaction provides a straightforward and practical access to cyano substituted pyrido[4,3,2- gh ]phenanthridines, and exhibits a good functional group tolerance. Furthermore, such methyl substituted polyheterocycles were also obtained through a similar radical cascade.</description><identifier>ISSN: 2052-4129</identifier><identifier>ISSN: 2052-4110</identifier><identifier>EISSN: 2052-4129</identifier><identifier>EISSN: 2052-4110</identifier><identifier>DOI: 10.1039/C8QO00336J</identifier><language>eng</language><publisher>London: Royal Society of Chemistry</publisher><subject>Acetonitrile ; Functional groups ; Organic chemistry ; Substitutes</subject><ispartof>Organic Chemistry Frontiers, 2018-06, Vol.5 (12), p.1945-1949</ispartof><rights>Copyright Royal Society of Chemistry 2018</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c259t-9edd28a688bea68d9aaedc20baadee009dccc2f454728034cfd56af6f576be983</citedby><cites>FETCH-LOGICAL-c259t-9edd28a688bea68d9aaedc20baadee009dccc2f454728034cfd56af6f576be983</cites><orcidid>0000-0003-4233-5274</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,27923,27924</link.rule.ids></links><search><creatorcontrib>Shang, Jia-Qi</creatorcontrib><creatorcontrib>Wang, Shi-Sheng</creatorcontrib><creatorcontrib>Fu, Hong</creatorcontrib><creatorcontrib>Li, Yi</creatorcontrib><creatorcontrib>Yang, Tao</creatorcontrib><creatorcontrib>Li, Ya-Min</creatorcontrib><title>Oxidative radical cascade cyclization involving C(sp 3 )–C(sp 3 ), C(sp 3 )–C(sp 2 ) and C(sp 2 )–N bonds formation: direct construction of cyano and methyl substituted polyheterocycles</title><title>Organic Chemistry Frontiers</title><description>An oxidative radical cascade cyclization of 2-cyano-3-arylaniline derived acrylamides with acetonitrile has been developed. The reaction provides a straightforward and practical access to cyano substituted pyrido[4,3,2- gh ]phenanthridines, and exhibits a good functional group tolerance. Furthermore, such methyl substituted polyheterocycles were also obtained through a similar radical cascade.</description><subject>Acetonitrile</subject><subject>Functional groups</subject><subject>Organic chemistry</subject><subject>Substitutes</subject><issn>2052-4129</issn><issn>2052-4110</issn><issn>2052-4129</issn><issn>2052-4110</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2018</creationdate><recordtype>article</recordtype><recordid>eNplUUtOwzAQjRBIVNANJxiJDUUEHCdOYnYo4quKCgnWkWM71FUaB9upCCvuwIG4CychbalAYjP_mTczz_MOAnQaoJCeZenDBKEwjO-2vAFGBPtRgOn2H3vXG1o7QwgFmMSIJAPvc_KqBHNqIcEwoTirgDPLmZDAO16ptz6na1D1QlcLVT9DdmQbCGH09f6xMU_-BTGMgNUCNk4fv4dC18JCqc18NfMchDKSO-C6ts60fAWkyx6X1XrVPpdu2lVg28I65VonBTS66qbSSaOX60m77-2UrLJy-KP3vKery8fsxh9Prm-zi7HPMaHOp1IInLI4TQvZS0EZk4JjVLD-UokQFZxzXEYkSnCKwoiXgsSsjEuSxIWkabjnHa7nNka_tNK6fKZbU_eQef_dkCCaRHFfdbyu4kZba2SZN0bNmenyAOVLjvJfjsJvPpCHXA</recordid><startdate>20180621</startdate><enddate>20180621</enddate><creator>Shang, Jia-Qi</creator><creator>Wang, Shi-Sheng</creator><creator>Fu, Hong</creator><creator>Li, Yi</creator><creator>Yang, Tao</creator><creator>Li, Ya-Min</creator><general>Royal Society of Chemistry</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7QO</scope><scope>7SR</scope><scope>8BQ</scope><scope>8FD</scope><scope>FR3</scope><scope>JG9</scope><scope>P64</scope><orcidid>https://orcid.org/0000-0003-4233-5274</orcidid></search><sort><creationdate>20180621</creationdate><title>Oxidative radical cascade cyclization involving C(sp 3 )–C(sp 3 ), C(sp 3 )–C(sp 2 ) and C(sp 2 )–N bonds formation: direct construction of cyano and methyl substituted polyheterocycles</title><author>Shang, Jia-Qi ; Wang, Shi-Sheng ; Fu, Hong ; Li, Yi ; Yang, Tao ; Li, Ya-Min</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c259t-9edd28a688bea68d9aaedc20baadee009dccc2f454728034cfd56af6f576be983</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2018</creationdate><topic>Acetonitrile</topic><topic>Functional groups</topic><topic>Organic chemistry</topic><topic>Substitutes</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Shang, Jia-Qi</creatorcontrib><creatorcontrib>Wang, Shi-Sheng</creatorcontrib><creatorcontrib>Fu, Hong</creatorcontrib><creatorcontrib>Li, Yi</creatorcontrib><creatorcontrib>Yang, Tao</creatorcontrib><creatorcontrib>Li, Ya-Min</creatorcontrib><collection>CrossRef</collection><collection>Biotechnology Research Abstracts</collection><collection>Engineered Materials Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Engineering Research Database</collection><collection>Materials Research Database</collection><collection>Biotechnology and BioEngineering Abstracts</collection><jtitle>Organic Chemistry Frontiers</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Shang, Jia-Qi</au><au>Wang, Shi-Sheng</au><au>Fu, Hong</au><au>Li, Yi</au><au>Yang, Tao</au><au>Li, Ya-Min</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Oxidative radical cascade cyclization involving C(sp 3 )–C(sp 3 ), C(sp 3 )–C(sp 2 ) and C(sp 2 )–N bonds formation: direct construction of cyano and methyl substituted polyheterocycles</atitle><jtitle>Organic Chemistry Frontiers</jtitle><date>2018-06-21</date><risdate>2018</risdate><volume>5</volume><issue>12</issue><spage>1945</spage><epage>1949</epage><pages>1945-1949</pages><issn>2052-4129</issn><issn>2052-4110</issn><eissn>2052-4129</eissn><eissn>2052-4110</eissn><abstract>An oxidative radical cascade cyclization of 2-cyano-3-arylaniline derived acrylamides with acetonitrile has been developed. The reaction provides a straightforward and practical access to cyano substituted pyrido[4,3,2- gh ]phenanthridines, and exhibits a good functional group tolerance. Furthermore, such methyl substituted polyheterocycles were also obtained through a similar radical cascade.</abstract><cop>London</cop><pub>Royal Society of Chemistry</pub><doi>10.1039/C8QO00336J</doi><tpages>5</tpages><orcidid>https://orcid.org/0000-0003-4233-5274</orcidid></addata></record>
fulltext fulltext
identifier ISSN: 2052-4129
ispartof Organic Chemistry Frontiers, 2018-06, Vol.5 (12), p.1945-1949
issn 2052-4129
2052-4110
2052-4129
2052-4110
language eng
recordid cdi_proquest_journals_2053509746
source Royal Society Of Chemistry Journals 2008-
subjects Acetonitrile
Functional groups
Organic chemistry
Substitutes
title Oxidative radical cascade cyclization involving C(sp 3 )–C(sp 3 ), C(sp 3 )–C(sp 2 ) and C(sp 2 )–N bonds formation: direct construction of cyano and methyl substituted polyheterocycles
url https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-11T18%3A06%3A12IST&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=Oxidative%20radical%20cascade%20cyclization%20involving%20C(sp%203%20)%E2%80%93C(sp%203%20),%20C(sp%203%20)%E2%80%93C(sp%202%20)%20and%20C(sp%202%20)%E2%80%93N%20bonds%20formation:%20direct%20construction%20of%20cyano%20and%20methyl%20substituted%20polyheterocycles&rft.jtitle=Organic%20Chemistry%20Frontiers&rft.au=Shang,%20Jia-Qi&rft.date=2018-06-21&rft.volume=5&rft.issue=12&rft.spage=1945&rft.epage=1949&rft.pages=1945-1949&rft.issn=2052-4129&rft.eissn=2052-4129&rft_id=info:doi/10.1039/C8QO00336J&rft_dat=%3Cproquest_cross%3E2053509746%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=2053509746&rft_id=info:pmid/&rfr_iscdi=true