Diversification of Quinazolinones by Pd-Catalyzed C(sp3)‑Acetoxylation

Diversification of Quinazolinones by Pd-Catalyzed C(sp3)‑Acetoxylation

The quinazolinone ring has been exploited as a directing group for C­(sp3)–H functionalization for the first time. The proximal C−γ­(sp3)–H bonds have been oxidized by palladium-catalyzed acetoxylation reaction. Various functional groups on the quinazolinone scaffold were tolerated to provide novel...

Ausführliche Beschreibung

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:Journal of organic chemistry 2017-10, Vol.82 (19), p.10470-10478
Hauptverfasser: Garad, Dnyaneshwar N, Mhaske, Santosh B
Format: Artikel
Sprache:eng
Online-Zugang:Volltext
Tags: Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
container_end_page 10478
container_issue 19
container_start_page 10470
container_title Journal of organic chemistry
container_volume 82
creator Garad, Dnyaneshwar N
Mhaske, Santosh B
description The quinazolinone ring has been exploited as a directing group for C­(sp3)–H functionalization for the first time. The proximal C−γ­(sp3)–H bonds have been oxidized by palladium-catalyzed acetoxylation reaction. Various functional groups on the quinazolinone scaffold were tolerated to provide novel quinazolinone derivatives. The use of base was found to be crucial for the monoselective acetoxylations.
doi_str_mv 10.1021/acs.joc.7b01934
format Article
fullrecord <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_1933232644</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>1933232644</sourcerecordid><originalsourceid>FETCH-LOGICAL-a333t-b107c85bbf9065997a911fdec04408c8fe1457afd5a1edee68be77a91ac0ea83</originalsourceid><addsrcrecordid>eNp1kL1OwzAUhS0EoqUws6GMRSitHdtNMlbhp0iVAKm75TjXkqs0LnGCSCdegVfkSXBJYeMud_nOkc6H0CXBE4IjMpXKTdZWTeIck5SyIzQkPMLhLMXsGA0xjqKQRjM6QGfOrbE_zvkpGkRJwniaxEO0uDVvUDujjZKNsVVgdfDSmkrubGkqW4EL8i54LsJMNrLsdlAE2dht6fXXx-dcQWPfu_IneI5OtCwdXBz-CK3u71bZIlw-PTxm82UoKaVNmBMcq4TnuU7xjKdpLFNCdAEKM4YTlWggjMdSF1wSKABmSQ7xHpIKg0zoCI372m1tX1twjdgYp6AsZQW2dcJboJGfzJhHpz2qautcDVpsa7ORdScIFnt7wtsT3p442POJq0N5m2-g-ON_dXngpgf6ZFtXfuq_dd-Ai3wT</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>1933232644</pqid></control><display><type>article</type><title>Diversification of Quinazolinones by Pd-Catalyzed C(sp3)‑Acetoxylation</title><source>American Chemical Society Journals</source><creator>Garad, Dnyaneshwar N ; Mhaske, Santosh B</creator><creatorcontrib>Garad, Dnyaneshwar N ; Mhaske, Santosh B</creatorcontrib><description>The quinazolinone ring has been exploited as a directing group for C­(sp3)–H functionalization for the first time. The proximal C−γ­(sp3)–H bonds have been oxidized by palladium-catalyzed acetoxylation reaction. Various functional groups on the quinazolinone scaffold were tolerated to provide novel quinazolinone derivatives. The use of base was found to be crucial for the monoselective acetoxylations.</description><identifier>ISSN: 0022-3263</identifier><identifier>EISSN: 1520-6904</identifier><identifier>DOI: 10.1021/acs.joc.7b01934</identifier><identifier>PMID: 28845987</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><ispartof>Journal of organic chemistry, 2017-10, Vol.82 (19), p.10470-10478</ispartof><rights>Copyright © 2017 American Chemical Society</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a333t-b107c85bbf9065997a911fdec04408c8fe1457afd5a1edee68be77a91ac0ea83</citedby><cites>FETCH-LOGICAL-a333t-b107c85bbf9065997a911fdec04408c8fe1457afd5a1edee68be77a91ac0ea83</cites><orcidid>0000-0002-5859-0838</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.7b01934$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/acs.joc.7b01934$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,780,784,2765,27076,27924,27925,56738,56788</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/28845987$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Garad, Dnyaneshwar N</creatorcontrib><creatorcontrib>Mhaske, Santosh B</creatorcontrib><title>Diversification of Quinazolinones by Pd-Catalyzed C(sp3)‑Acetoxylation</title><title>Journal of organic chemistry</title><addtitle>J. Org. Chem</addtitle><description>The quinazolinone ring has been exploited as a directing group for C­(sp3)–H functionalization for the first time. The proximal C−γ­(sp3)–H bonds have been oxidized by palladium-catalyzed acetoxylation reaction. Various functional groups on the quinazolinone scaffold were tolerated to provide novel quinazolinone derivatives. The use of base was found to be crucial for the monoselective acetoxylations.</description><issn>0022-3263</issn><issn>1520-6904</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2017</creationdate><recordtype>article</recordtype><recordid>eNp1kL1OwzAUhS0EoqUws6GMRSitHdtNMlbhp0iVAKm75TjXkqs0LnGCSCdegVfkSXBJYeMud_nOkc6H0CXBE4IjMpXKTdZWTeIck5SyIzQkPMLhLMXsGA0xjqKQRjM6QGfOrbE_zvkpGkRJwniaxEO0uDVvUDujjZKNsVVgdfDSmkrubGkqW4EL8i54LsJMNrLsdlAE2dht6fXXx-dcQWPfu_IneI5OtCwdXBz-CK3u71bZIlw-PTxm82UoKaVNmBMcq4TnuU7xjKdpLFNCdAEKM4YTlWggjMdSF1wSKABmSQ7xHpIKg0zoCI372m1tX1twjdgYp6AsZQW2dcJboJGfzJhHpz2qautcDVpsa7ORdScIFnt7wtsT3p442POJq0N5m2-g-ON_dXngpgf6ZFtXfuq_dd-Ai3wT</recordid><startdate>20171006</startdate><enddate>20171006</enddate><creator>Garad, Dnyaneshwar N</creator><creator>Mhaske, Santosh B</creator><general>American Chemical Society</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0002-5859-0838</orcidid></search><sort><creationdate>20171006</creationdate><title>Diversification of Quinazolinones by Pd-Catalyzed C(sp3)‑Acetoxylation</title><author>Garad, Dnyaneshwar N ; Mhaske, Santosh B</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a333t-b107c85bbf9065997a911fdec04408c8fe1457afd5a1edee68be77a91ac0ea83</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2017</creationdate><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Garad, Dnyaneshwar N</creatorcontrib><creatorcontrib>Mhaske, Santosh B</creatorcontrib><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>Garad, Dnyaneshwar N</au><au>Mhaske, Santosh B</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Diversification of Quinazolinones by Pd-Catalyzed C(sp3)‑Acetoxylation</atitle><jtitle>Journal of organic chemistry</jtitle><addtitle>J. Org. Chem</addtitle><date>2017-10-06</date><risdate>2017</risdate><volume>82</volume><issue>19</issue><spage>10470</spage><epage>10478</epage><pages>10470-10478</pages><issn>0022-3263</issn><eissn>1520-6904</eissn><abstract>The quinazolinone ring has been exploited as a directing group for C­(sp3)–H functionalization for the first time. The proximal C−γ­(sp3)–H bonds have been oxidized by palladium-catalyzed acetoxylation reaction. Various functional groups on the quinazolinone scaffold were tolerated to provide novel quinazolinone derivatives. The use of base was found to be crucial for the monoselective acetoxylations.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>28845987</pmid><doi>10.1021/acs.joc.7b01934</doi><tpages>9</tpages><orcidid>https://orcid.org/0000-0002-5859-0838</orcidid></addata></record>
fulltext fulltext
identifier ISSN: 0022-3263
ispartof Journal of organic chemistry, 2017-10, Vol.82 (19), p.10470-10478
issn 0022-3263
1520-6904
language eng
recordid cdi_proquest_miscellaneous_1933232644
source American Chemical Society Journals
title Diversification of Quinazolinones by Pd-Catalyzed C(sp3)‑Acetoxylation
url https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2024-12-28T13%3A43%3A32IST&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=Diversification%20of%20Quinazolinones%20by%20Pd-Catalyzed%20C(sp3)%E2%80%91Acetoxylation&rft.jtitle=Journal%20of%20organic%20chemistry&rft.au=Garad,%20Dnyaneshwar%20N&rft.date=2017-10-06&rft.volume=82&rft.issue=19&rft.spage=10470&rft.epage=10478&rft.pages=10470-10478&rft.issn=0022-3263&rft.eissn=1520-6904&rft_id=info:doi/10.1021/acs.joc.7b01934&rft_dat=%3Cproquest_cross%3E1933232644%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=1933232644&rft_id=info:pmid/28845987&rfr_iscdi=true