Copper-catalyzed oxidative amination of methanol to access quinazolines

A novel method for the copper-catalyzed oxidative amination of 2′-aminoarylketones with methanol as a C1 carbon source and ammonium acetate as an amine source to construct quinazolines was established in a one-pot manner. The reaction conditions are straightforward and highly atom economic to delive...

Ausführliche Beschreibung

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:Organic & biomolecular chemistry 2019-05, Vol.17 (19), p.4774-4782
Hauptverfasser: Satish, Gandhesiri, Polu, Ashok, Kota, Laxman, Ilangovan, Andivelu
Format: Artikel
Sprache:eng
Online-Zugang:Volltext
Tags: Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
container_end_page 4782
container_issue 19
container_start_page 4774
container_title Organic & biomolecular chemistry
container_volume 17
creator Satish, Gandhesiri
Polu, Ashok
Kota, Laxman
Ilangovan, Andivelu
description A novel method for the copper-catalyzed oxidative amination of 2′-aminoarylketones with methanol as a C1 carbon source and ammonium acetate as an amine source to construct quinazolines was established in a one-pot manner. The reaction conditions are straightforward and highly atom economic to deliver the corresponding quinazolines in high yields with wide functional group tolerance. Importantly, the present method is applicable on a multigram scale and its synthetic utility is demonstrated by synthesizing quazodine, a muscle-relaxing drug in high yields. A novel method for the copper-catalyzed oxidative amination of 2′-aminoarylketones with methanol as a C1 carbon source and ammonium acetate as an amine source to construct quinazolines was established in a one-pot manner.
doi_str_mv 10.1039/c9ob00392d
format Article
fullrecord <record><control><sourceid>proquest_pubme</sourceid><recordid>TN_cdi_pubmed_primary_31033980</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>2216776319</sourcerecordid><originalsourceid>FETCH-LOGICAL-c350t-90acb48f5341310e7fd2bbd4a76b1cc7efba13f83f03ccc97a30aebaa6d345cf3</originalsourceid><addsrcrecordid>eNpFkMFLwzAUh4Mobk4v3pUeRagmTdssR606hcEuei4vrwlW2qZrWnH76412ztP7wfvej8dHyDmjN4xyeYvSKupDVByQKYuFCGnC5eE-R3RCTpz7oJRJkcbHZML9HZdzOiWLzLat7kKEHqrNVheB_SoL6MtPHUBdNj7ZJrAmqHX_Do2tgt4GgKidC9aD329tVTbanZIjA5XTZ7s5I29Pj6_Zc7hcLV6yu2WIPKF9KCmgiucm4THzT2hhikipIgaRKoYotFHAuJlzQzkiSgGcglYAacHjBA2fkauxt-3setCuz-vSoa4qaLQdXB5FLBUi5Ux69HpEsbPOddrkbVfW0G1yRvMfcXkmV_e_4h48fLnrHVStiz36Z8oDFyPQOdxv_83zbwNvdBI</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>2216776319</pqid></control><display><type>article</type><title>Copper-catalyzed oxidative amination of methanol to access quinazolines</title><source>Royal Society Of Chemistry Journals 2008-</source><source>Alma/SFX Local Collection</source><creator>Satish, Gandhesiri ; Polu, Ashok ; Kota, Laxman ; Ilangovan, Andivelu</creator><creatorcontrib>Satish, Gandhesiri ; Polu, Ashok ; Kota, Laxman ; Ilangovan, Andivelu</creatorcontrib><description>A novel method for the copper-catalyzed oxidative amination of 2′-aminoarylketones with methanol as a C1 carbon source and ammonium acetate as an amine source to construct quinazolines was established in a one-pot manner. The reaction conditions are straightforward and highly atom economic to deliver the corresponding quinazolines in high yields with wide functional group tolerance. Importantly, the present method is applicable on a multigram scale and its synthetic utility is demonstrated by synthesizing quazodine, a muscle-relaxing drug in high yields. A novel method for the copper-catalyzed oxidative amination of 2′-aminoarylketones with methanol as a C1 carbon source and ammonium acetate as an amine source to construct quinazolines was established in a one-pot manner.</description><identifier>ISSN: 1477-0520</identifier><identifier>EISSN: 1477-0539</identifier><identifier>DOI: 10.1039/c9ob00392d</identifier><identifier>PMID: 31033980</identifier><language>eng</language><publisher>England</publisher><ispartof>Organic &amp; biomolecular chemistry, 2019-05, Vol.17 (19), p.4774-4782</ispartof><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c350t-90acb48f5341310e7fd2bbd4a76b1cc7efba13f83f03ccc97a30aebaa6d345cf3</citedby><cites>FETCH-LOGICAL-c350t-90acb48f5341310e7fd2bbd4a76b1cc7efba13f83f03ccc97a30aebaa6d345cf3</cites><orcidid>0000-0003-2703-8562</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,776,780,27901,27902</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/31033980$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Satish, Gandhesiri</creatorcontrib><creatorcontrib>Polu, Ashok</creatorcontrib><creatorcontrib>Kota, Laxman</creatorcontrib><creatorcontrib>Ilangovan, Andivelu</creatorcontrib><title>Copper-catalyzed oxidative amination of methanol to access quinazolines</title><title>Organic &amp; biomolecular chemistry</title><addtitle>Org Biomol Chem</addtitle><description>A novel method for the copper-catalyzed oxidative amination of 2′-aminoarylketones with methanol as a C1 carbon source and ammonium acetate as an amine source to construct quinazolines was established in a one-pot manner. The reaction conditions are straightforward and highly atom economic to deliver the corresponding quinazolines in high yields with wide functional group tolerance. Importantly, the present method is applicable on a multigram scale and its synthetic utility is demonstrated by synthesizing quazodine, a muscle-relaxing drug in high yields. A novel method for the copper-catalyzed oxidative amination of 2′-aminoarylketones with methanol as a C1 carbon source and ammonium acetate as an amine source to construct quinazolines was established in a one-pot manner.</description><issn>1477-0520</issn><issn>1477-0539</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2019</creationdate><recordtype>article</recordtype><recordid>eNpFkMFLwzAUh4Mobk4v3pUeRagmTdssR606hcEuei4vrwlW2qZrWnH76412ztP7wfvej8dHyDmjN4xyeYvSKupDVByQKYuFCGnC5eE-R3RCTpz7oJRJkcbHZML9HZdzOiWLzLat7kKEHqrNVheB_SoL6MtPHUBdNj7ZJrAmqHX_Do2tgt4GgKidC9aD329tVTbanZIjA5XTZ7s5I29Pj6_Zc7hcLV6yu2WIPKF9KCmgiucm4THzT2hhikipIgaRKoYotFHAuJlzQzkiSgGcglYAacHjBA2fkauxt-3setCuz-vSoa4qaLQdXB5FLBUi5Ux69HpEsbPOddrkbVfW0G1yRvMfcXkmV_e_4h48fLnrHVStiz36Z8oDFyPQOdxv_83zbwNvdBI</recordid><startdate>20190515</startdate><enddate>20190515</enddate><creator>Satish, Gandhesiri</creator><creator>Polu, Ashok</creator><creator>Kota, Laxman</creator><creator>Ilangovan, Andivelu</creator><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0003-2703-8562</orcidid></search><sort><creationdate>20190515</creationdate><title>Copper-catalyzed oxidative amination of methanol to access quinazolines</title><author>Satish, Gandhesiri ; Polu, Ashok ; Kota, Laxman ; Ilangovan, Andivelu</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c350t-90acb48f5341310e7fd2bbd4a76b1cc7efba13f83f03ccc97a30aebaa6d345cf3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2019</creationdate><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Satish, Gandhesiri</creatorcontrib><creatorcontrib>Polu, Ashok</creatorcontrib><creatorcontrib>Kota, Laxman</creatorcontrib><creatorcontrib>Ilangovan, Andivelu</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Organic &amp; biomolecular chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Satish, Gandhesiri</au><au>Polu, Ashok</au><au>Kota, Laxman</au><au>Ilangovan, Andivelu</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Copper-catalyzed oxidative amination of methanol to access quinazolines</atitle><jtitle>Organic &amp; biomolecular chemistry</jtitle><addtitle>Org Biomol Chem</addtitle><date>2019-05-15</date><risdate>2019</risdate><volume>17</volume><issue>19</issue><spage>4774</spage><epage>4782</epage><pages>4774-4782</pages><issn>1477-0520</issn><eissn>1477-0539</eissn><abstract>A novel method for the copper-catalyzed oxidative amination of 2′-aminoarylketones with methanol as a C1 carbon source and ammonium acetate as an amine source to construct quinazolines was established in a one-pot manner. The reaction conditions are straightforward and highly atom economic to deliver the corresponding quinazolines in high yields with wide functional group tolerance. Importantly, the present method is applicable on a multigram scale and its synthetic utility is demonstrated by synthesizing quazodine, a muscle-relaxing drug in high yields. A novel method for the copper-catalyzed oxidative amination of 2′-aminoarylketones with methanol as a C1 carbon source and ammonium acetate as an amine source to construct quinazolines was established in a one-pot manner.</abstract><cop>England</cop><pmid>31033980</pmid><doi>10.1039/c9ob00392d</doi><tpages>9</tpages><orcidid>https://orcid.org/0000-0003-2703-8562</orcidid></addata></record>
fulltext fulltext
identifier ISSN: 1477-0520
ispartof Organic & biomolecular chemistry, 2019-05, Vol.17 (19), p.4774-4782
issn 1477-0520
1477-0539
language eng
recordid cdi_pubmed_primary_31033980
source Royal Society Of Chemistry Journals 2008-; Alma/SFX Local Collection
title Copper-catalyzed oxidative amination of methanol to access quinazolines
url https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-02-05T23%3A51%3A07IST&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=Copper-catalyzed%20oxidative%20amination%20of%20methanol%20to%20access%20quinazolines&rft.jtitle=Organic%20&%20biomolecular%20chemistry&rft.au=Satish,%20Gandhesiri&rft.date=2019-05-15&rft.volume=17&rft.issue=19&rft.spage=4774&rft.epage=4782&rft.pages=4774-4782&rft.issn=1477-0520&rft.eissn=1477-0539&rft_id=info:doi/10.1039/c9ob00392d&rft_dat=%3Cproquest_pubme%3E2216776319%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=2216776319&rft_id=info:pmid/31033980&rfr_iscdi=true