Synthesis of Cu-catalysed quinazolinones using a Csp3-H functionalisation/cyclisation strategy

Synthesis of Cu-catalysed quinazolinones using a Csp3-H functionalisation/cyclisation strategy

A series of 2,3-disubstituted-4(3H)-quinazolinones were synthesised via a copper-catalysed Csp3-H functionalisation/cyclisation of 2-amino-N,N-dialkylbenzamides. In comparison to the reported methods this strategy allows an easy access to diversely substituted quinazolinones under mild conditions in...

Ausführliche Beschreibung

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:Organic & biomolecular chemistry 2017-08, Vol.15 (34), p.7140-7146
Hauptverfasser: Gholap, Aniket V A, Maity, Soham, Schulzke, Carola, Maiti, Debabrata, Kapdi, Anant R
Format: Artikel
Sprache:eng
Online-Zugang:Volltext
Tags: Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
container_end_page 7146
container_issue 34
container_start_page 7140
container_title Organic & biomolecular chemistry
container_volume 15
creator Gholap, Aniket V A
Maity, Soham
Schulzke, Carola
Maiti, Debabrata
Kapdi, Anant R
description A series of 2,3-disubstituted-4(3H)-quinazolinones were synthesised via a copper-catalysed Csp3-H functionalisation/cyclisation of 2-amino-N,N-dialkylbenzamides. In comparison to the reported methods this strategy allows an easy access to diversely substituted quinazolinones under mild conditions in air. The reaction also exhibits good functional group tolerance and would be of value to heterocyclic researchers as well as pharmaceutical process chemists. The reaction is proposed to proceed through a double SET type radical mechanism.
doi_str_mv 10.1039/c7ob01723e
format Article
fullrecord <record><control><sourceid>proquest</sourceid><recordid>TN_cdi_proquest_miscellaneous_1928785938</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>1928785938</sourcerecordid><originalsourceid>FETCH-LOGICAL-p103t-eb5bf4a56aeb748452658591cf698c196558fa78c6187420306310c76ec1c2d3</originalsourceid><addsrcrecordid>eNo1jj9PAyEcQImJibW6-AkYXc7C8X80F7UmTRzsbMNRqBiEtj8Yzk9vjTq9N708hG4ouaOEmYVTZSRU9cyfoRnlSnVEMHOBLgE-CKFGST5Db69Tru8eIuAS8NA6Z6tNE_gtPrSY7VdJMZfsATeIeYctHmDPuiUOLbsaS7Ypgv2RhZvcv2OoR1v9brpC58Em8Nd_nKP148N6WHarl6fn4X7V7U-rtfOjGAO3Qlo_Kq656KXQwlAXpNGOGimEDlZpJ6lWvCeMSEaJU9I76votm6Pb3-z-WA7NQ918RnA-JZt9abChptfqFGSafQME2VXt</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>1928785938</pqid></control><display><type>article</type><title>Synthesis of Cu-catalysed quinazolinones using a Csp3-H functionalisation/cyclisation strategy</title><source>Alma/SFX Local Collection</source><source>Royal Society of Chemistry E-Journals</source><creator>Gholap, Aniket V A ; Maity, Soham ; Schulzke, Carola ; Maiti, Debabrata ; Kapdi, Anant R</creator><creatorcontrib>Gholap, Aniket V A ; Maity, Soham ; Schulzke, Carola ; Maiti, Debabrata ; Kapdi, Anant R</creatorcontrib><description>A series of 2,3-disubstituted-4(3H)-quinazolinones were synthesised via a copper-catalysed Csp3-H functionalisation/cyclisation of 2-amino-N,N-dialkylbenzamides. In comparison to the reported methods this strategy allows an easy access to diversely substituted quinazolinones under mild conditions in air. The reaction also exhibits good functional group tolerance and would be of value to heterocyclic researchers as well as pharmaceutical process chemists. The reaction is proposed to proceed through a double SET type radical mechanism.</description><identifier>EISSN: 1477-0539</identifier><identifier>DOI: 10.1039/c7ob01723e</identifier><language>eng</language><ispartof>Organic &amp; biomolecular chemistry, 2017-08, Vol.15 (34), p.7140-7146</ispartof><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,776,780,27903,27904</link.rule.ids></links><search><creatorcontrib>Gholap, Aniket V A</creatorcontrib><creatorcontrib>Maity, Soham</creatorcontrib><creatorcontrib>Schulzke, Carola</creatorcontrib><creatorcontrib>Maiti, Debabrata</creatorcontrib><creatorcontrib>Kapdi, Anant R</creatorcontrib><title>Synthesis of Cu-catalysed quinazolinones using a Csp3-H functionalisation/cyclisation strategy</title><title>Organic &amp; biomolecular chemistry</title><description>A series of 2,3-disubstituted-4(3H)-quinazolinones were synthesised via a copper-catalysed Csp3-H functionalisation/cyclisation of 2-amino-N,N-dialkylbenzamides. In comparison to the reported methods this strategy allows an easy access to diversely substituted quinazolinones under mild conditions in air. The reaction also exhibits good functional group tolerance and would be of value to heterocyclic researchers as well as pharmaceutical process chemists. The reaction is proposed to proceed through a double SET type radical mechanism.</description><issn>1477-0539</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2017</creationdate><recordtype>article</recordtype><recordid>eNo1jj9PAyEcQImJibW6-AkYXc7C8X80F7UmTRzsbMNRqBiEtj8Yzk9vjTq9N708hG4ouaOEmYVTZSRU9cyfoRnlSnVEMHOBLgE-CKFGST5Db69Tru8eIuAS8NA6Z6tNE_gtPrSY7VdJMZfsATeIeYctHmDPuiUOLbsaS7Ypgv2RhZvcv2OoR1v9brpC58Em8Nd_nKP148N6WHarl6fn4X7V7U-rtfOjGAO3Qlo_Kq656KXQwlAXpNGOGimEDlZpJ6lWvCeMSEaJU9I76votm6Pb3-z-WA7NQ918RnA-JZt9abChptfqFGSafQME2VXt</recordid><startdate>20170830</startdate><enddate>20170830</enddate><creator>Gholap, Aniket V A</creator><creator>Maity, Soham</creator><creator>Schulzke, Carola</creator><creator>Maiti, Debabrata</creator><creator>Kapdi, Anant R</creator><scope>7X8</scope></search><sort><creationdate>20170830</creationdate><title>Synthesis of Cu-catalysed quinazolinones using a Csp3-H functionalisation/cyclisation strategy</title><author>Gholap, Aniket V A ; Maity, Soham ; Schulzke, Carola ; Maiti, Debabrata ; Kapdi, Anant R</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-p103t-eb5bf4a56aeb748452658591cf698c196558fa78c6187420306310c76ec1c2d3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2017</creationdate><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Gholap, Aniket V A</creatorcontrib><creatorcontrib>Maity, Soham</creatorcontrib><creatorcontrib>Schulzke, Carola</creatorcontrib><creatorcontrib>Maiti, Debabrata</creatorcontrib><creatorcontrib>Kapdi, Anant R</creatorcontrib><collection>MEDLINE - Academic</collection><jtitle>Organic &amp; biomolecular chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Gholap, Aniket V A</au><au>Maity, Soham</au><au>Schulzke, Carola</au><au>Maiti, Debabrata</au><au>Kapdi, Anant R</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis of Cu-catalysed quinazolinones using a Csp3-H functionalisation/cyclisation strategy</atitle><jtitle>Organic &amp; biomolecular chemistry</jtitle><date>2017-08-30</date><risdate>2017</risdate><volume>15</volume><issue>34</issue><spage>7140</spage><epage>7146</epage><pages>7140-7146</pages><eissn>1477-0539</eissn><abstract>A series of 2,3-disubstituted-4(3H)-quinazolinones were synthesised via a copper-catalysed Csp3-H functionalisation/cyclisation of 2-amino-N,N-dialkylbenzamides. In comparison to the reported methods this strategy allows an easy access to diversely substituted quinazolinones under mild conditions in air. The reaction also exhibits good functional group tolerance and would be of value to heterocyclic researchers as well as pharmaceutical process chemists. The reaction is proposed to proceed through a double SET type radical mechanism.</abstract><doi>10.1039/c7ob01723e</doi><tpages>7</tpages></addata></record>
fulltext fulltext
identifier EISSN: 1477-0539
ispartof Organic & biomolecular chemistry, 2017-08, Vol.15 (34), p.7140-7146
issn 1477-0539
language eng
recordid cdi_proquest_miscellaneous_1928785938
source Alma/SFX Local Collection; Royal Society of Chemistry E-Journals
title Synthesis of Cu-catalysed quinazolinones using a Csp3-H functionalisation/cyclisation strategy
url https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-22T16%3A17%3A44IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Synthesis%20of%20Cu-catalysed%20quinazolinones%20using%20a%20Csp3-H%20functionalisation/cyclisation%20strategy&rft.jtitle=Organic%20&%20biomolecular%20chemistry&rft.au=Gholap,%20Aniket%20V%20A&rft.date=2017-08-30&rft.volume=15&rft.issue=34&rft.spage=7140&rft.epage=7146&rft.pages=7140-7146&rft.eissn=1477-0539&rft_id=info:doi/10.1039/c7ob01723e&rft_dat=%3Cproquest%3E1928785938%3C/proquest%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_pqid=1928785938&rft_id=info:pmid/&rfr_iscdi=true