Regioselective synthesis of N(3)- and O-acylmethyl derivatives of 2-methylthio-4(3H)-quinazolinone

Regioselective synthesis of N(3)- and O-acylmethyl derivatives of 2-methylthio-4(3H)-quinazolinone

Reaction of 2‐methylthio‐4(3H)‐quinazolinone with chloroacetone, ω‐bromoacetophenone or ethyl bromoacetate in different solvents (methanol, acetonitrile, dimethylformamide and toluene) using sodium methoxide or potassium carbonate as a base were studied. Regioselective N(3)‐alkylation took place in...

Ausführliche Beschreibung

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:Journal of heterocyclic chemistry 2008-03, Vol.45 (2), p.607-610
Hauptverfasser: Burbuliene, Milda M., Mazeikaite, Rita, Vainilavicius, Povilas
Format: Artikel
Sprache:eng
Online-Zugang:Volltext
Tags: Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
container_end_page 610
container_issue 2
container_start_page 607
container_title Journal of heterocyclic chemistry
container_volume 45
creator Burbuliene, Milda M.
Mazeikaite, Rita
Vainilavicius, Povilas
description Reaction of 2‐methylthio‐4(3H)‐quinazolinone with chloroacetone, ω‐bromoacetophenone or ethyl bromoacetate in different solvents (methanol, acetonitrile, dimethylformamide and toluene) using sodium methoxide or potassium carbonate as a base were studied. Regioselective N(3)‐alkylation took place in toluene using potassium carbonate, whereas in dimethylformamide O‐acylmethyl derivatives were obtained. However chloroacetone reacted with 2‐methylthio‐4(3H)‐quinazolinone under various conditions to give a mixture of N(3)/O‐isomers.
doi_str_mv 10.1002/jhet.5570450250
format Article
fullrecord <record><control><sourceid>istex_cross</sourceid><recordid>TN_cdi_crossref_primary_10_1002_jhet_5570450250</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>ark_67375_WNG_CGLMDFTB_S</sourcerecordid><originalsourceid>FETCH-LOGICAL-c3310-122128c2840aa6f5222119652f616d2d519bfb46a4b7cb04912668aa984a7f03</originalsourceid><addsrcrecordid>eNqFkE1Pg0AURSdGE2t17ZZlu5h2voG40toWTW0TJdHdZIBBplJQBqv466ViNK5cvdyXc17yLgCnGI0wQmS8znQ94txFjCPC0R7oYZ9RyLFP90GvJQjEnDwcgiNr123E1HV7ILrVj6a0OtdxbbbasU1RZ9oa65SpsxzQIXRUkTgrqOIm3-g6a3In0ZXZqh3-RRHY7evMlJANaDCEL6-mUB9lboqy0MfgIFW51Sffsw_C2TScBHCxml9NzhcwphQjiAnBxIuJx5BSIuWkzdgXnKQCi4Qk7SNRGjGhWOTGEWI-JkJ4SvkeU26KaB-Mu7NxVVpb6VQ-V2ajqkZiJHcNyV1D8reh1jjrjDeT6-Y_XF4H0_CPDTvb2Fq__9iqepLCpS6X98u5nMwXN5ez8ELe0U_kmHmd</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype></control><display><type>article</type><title>Regioselective synthesis of N(3)- and O-acylmethyl derivatives of 2-methylthio-4(3H)-quinazolinone</title><source>Access via Wiley Online Library</source><creator>Burbuliene, Milda M. ; Mazeikaite, Rita ; Vainilavicius, Povilas</creator><creatorcontrib>Burbuliene, Milda M. ; Mazeikaite, Rita ; Vainilavicius, Povilas</creatorcontrib><description>Reaction of 2‐methylthio‐4(3H)‐quinazolinone with chloroacetone, ω‐bromoacetophenone or ethyl bromoacetate in different solvents (methanol, acetonitrile, dimethylformamide and toluene) using sodium methoxide or potassium carbonate as a base were studied. Regioselective N(3)‐alkylation took place in toluene using potassium carbonate, whereas in dimethylformamide O‐acylmethyl derivatives were obtained. However chloroacetone reacted with 2‐methylthio‐4(3H)‐quinazolinone under various conditions to give a mixture of N(3)/O‐isomers.</description><identifier>ISSN: 0022-152X</identifier><identifier>EISSN: 1943-5193</identifier><identifier>DOI: 10.1002/jhet.5570450250</identifier><language>eng</language><publisher>Hoboken: Wiley-Blackwell</publisher><ispartof>Journal of heterocyclic chemistry, 2008-03, Vol.45 (2), p.607-610</ispartof><rights>Copyright © 2008 Journal of Heterocyclic Chemistry</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c3310-122128c2840aa6f5222119652f616d2d519bfb46a4b7cb04912668aa984a7f03</citedby><cites>FETCH-LOGICAL-c3310-122128c2840aa6f5222119652f616d2d519bfb46a4b7cb04912668aa984a7f03</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fjhet.5570450250$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fjhet.5570450250$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,780,784,1417,27924,27925,45574,45575</link.rule.ids></links><search><creatorcontrib>Burbuliene, Milda M.</creatorcontrib><creatorcontrib>Mazeikaite, Rita</creatorcontrib><creatorcontrib>Vainilavicius, Povilas</creatorcontrib><title>Regioselective synthesis of N(3)- and O-acylmethyl derivatives of 2-methylthio-4(3H)-quinazolinone</title><title>Journal of heterocyclic chemistry</title><description>Reaction of 2‐methylthio‐4(3H)‐quinazolinone with chloroacetone, ω‐bromoacetophenone or ethyl bromoacetate in different solvents (methanol, acetonitrile, dimethylformamide and toluene) using sodium methoxide or potassium carbonate as a base were studied. Regioselective N(3)‐alkylation took place in toluene using potassium carbonate, whereas in dimethylformamide O‐acylmethyl derivatives were obtained. However chloroacetone reacted with 2‐methylthio‐4(3H)‐quinazolinone under various conditions to give a mixture of N(3)/O‐isomers.</description><issn>0022-152X</issn><issn>1943-5193</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2008</creationdate><recordtype>article</recordtype><recordid>eNqFkE1Pg0AURSdGE2t17ZZlu5h2voG40toWTW0TJdHdZIBBplJQBqv466ViNK5cvdyXc17yLgCnGI0wQmS8znQ94txFjCPC0R7oYZ9RyLFP90GvJQjEnDwcgiNr123E1HV7ILrVj6a0OtdxbbbasU1RZ9oa65SpsxzQIXRUkTgrqOIm3-g6a3In0ZXZqh3-RRHY7evMlJANaDCEL6-mUB9lboqy0MfgIFW51Sffsw_C2TScBHCxml9NzhcwphQjiAnBxIuJx5BSIuWkzdgXnKQCi4Qk7SNRGjGhWOTGEWI-JkJ4SvkeU26KaB-Mu7NxVVpb6VQ-V2ajqkZiJHcNyV1D8reh1jjrjDeT6-Y_XF4H0_CPDTvb2Fq__9iqepLCpS6X98u5nMwXN5ez8ELe0U_kmHmd</recordid><startdate>200803</startdate><enddate>200803</enddate><creator>Burbuliene, Milda M.</creator><creator>Mazeikaite, Rita</creator><creator>Vainilavicius, Povilas</creator><general>Wiley-Blackwell</general><general>Wiley‐Blackwell</general><scope>BSCLL</scope><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>200803</creationdate><title>Regioselective synthesis of N(3)- and O-acylmethyl derivatives of 2-methylthio-4(3H)-quinazolinone</title><author>Burbuliene, Milda M. ; Mazeikaite, Rita ; Vainilavicius, Povilas</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3310-122128c2840aa6f5222119652f616d2d519bfb46a4b7cb04912668aa984a7f03</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2008</creationdate><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Burbuliene, Milda M.</creatorcontrib><creatorcontrib>Mazeikaite, Rita</creatorcontrib><creatorcontrib>Vainilavicius, Povilas</creatorcontrib><collection>Istex</collection><collection>CrossRef</collection><jtitle>Journal of heterocyclic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Burbuliene, Milda M.</au><au>Mazeikaite, Rita</au><au>Vainilavicius, Povilas</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Regioselective synthesis of N(3)- and O-acylmethyl derivatives of 2-methylthio-4(3H)-quinazolinone</atitle><jtitle>Journal of heterocyclic chemistry</jtitle><date>2008-03</date><risdate>2008</risdate><volume>45</volume><issue>2</issue><spage>607</spage><epage>610</epage><pages>607-610</pages><issn>0022-152X</issn><eissn>1943-5193</eissn><abstract>Reaction of 2‐methylthio‐4(3H)‐quinazolinone with chloroacetone, ω‐bromoacetophenone or ethyl bromoacetate in different solvents (methanol, acetonitrile, dimethylformamide and toluene) using sodium methoxide or potassium carbonate as a base were studied. Regioselective N(3)‐alkylation took place in toluene using potassium carbonate, whereas in dimethylformamide O‐acylmethyl derivatives were obtained. However chloroacetone reacted with 2‐methylthio‐4(3H)‐quinazolinone under various conditions to give a mixture of N(3)/O‐isomers.</abstract><cop>Hoboken</cop><pub>Wiley-Blackwell</pub><doi>10.1002/jhet.5570450250</doi><tpages>4</tpages></addata></record>
fulltext fulltext
identifier ISSN: 0022-152X
ispartof Journal of heterocyclic chemistry, 2008-03, Vol.45 (2), p.607-610
issn 0022-152X
1943-5193
language eng
recordid cdi_crossref_primary_10_1002_jhet_5570450250
source Access via Wiley Online Library
title Regioselective synthesis of N(3)- and O-acylmethyl derivatives of 2-methylthio-4(3H)-quinazolinone
url https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2024-12-30T17%3A15%3A19IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-istex_cross&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Regioselective%20synthesis%20of%20N(3)-%20and%20O-acylmethyl%20derivatives%20of%202-methylthio-4(3H)-quinazolinone&rft.jtitle=Journal%20of%20heterocyclic%20chemistry&rft.au=Burbuliene,%20Milda%20M.&rft.date=2008-03&rft.volume=45&rft.issue=2&rft.spage=607&rft.epage=610&rft.pages=607-610&rft.issn=0022-152X&rft.eissn=1943-5193&rft_id=info:doi/10.1002/jhet.5570450250&rft_dat=%3Cistex_cross%3Eark_67375_WNG_CGLMDFTB_S%3C/istex_cross%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_id=info:pmid/&rfr_iscdi=true