A solvent-free and catalyst-free reaction of o-aminobenzophenone with aryl isothiocyanates: expedient access to congested 4-phenyl-4-hydroxyquinazolin-2-thione derivatives†
Le Anh Nguyen , Thi Thu Tram Nguyen , Quoc Anh Ngo , Pascal Retailleau , Thanh Binh Nguyen
{"title":"A solvent-free and catalyst-free reaction of o-aminobenzophenone with aryl isothiocyanates: expedient access to congested 4-phenyl-4-hydroxyquinazolin-2-thione derivatives†","authors":"Le Anh Nguyen , Thi Thu Tram Nguyen , Quoc Anh Ngo , Pascal Retailleau , Thanh Binh Nguyen","doi":"10.1039/d4ob01452a","DOIUrl":null,"url":null,"abstract":"<div><div>An efficient method to construct 4-phenyl-4-hydroxyquinazolin-2-thiones <em>via</em> solvent-free and catalyst-free addition of <em>o</em>-aminobenzophenone with aryl isothiocyanates under thermal conditions has been developed, providing new congested 4-phenyl-4-hydroxyquinazolin-2-thiones in practically quantitative yields <em>via</em> simple purification by filtration/recrystallization. Extension of these conditions to <em>o</em>-aminoacetophenone in place of <em>o</em>-aminobenzophenone led to 4-methylenequinazoline-thione as a result of a subsequent dehydration reaction.</div></div>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":"22 48","pages":"Pages 9353-9356"},"PeriodicalIF":2.7000,"publicationDate":"2024-10-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Organic & Biomolecular Chemistry","FirstCategoryId":"92","ListUrlMain":"https://www.sciencedirect.com/org/science/article/pii/S1477052024009510","RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"2024/10/28 0:00:00","PubModel":"Epub","JCR":"Q1","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
引用次数: 0
Abstract
An efficient method to construct 4-phenyl-4-hydroxyquinazolin-2-thiones via solvent-free and catalyst-free addition of o-aminobenzophenone with aryl isothiocyanates under thermal conditions has been developed, providing new congested 4-phenyl-4-hydroxyquinazolin-2-thiones in practically quantitative yields via simple purification by filtration/recrystallization. Extension of these conditions to o-aminoacetophenone in place of o-aminobenzophenone led to 4-methylenequinazoline-thione as a result of a subsequent dehydration reaction.
期刊介绍:
Organic & Biomolecular Chemistry is an international journal using integrated research in chemistry-organic chemistry. Founded in 2003 by the Royal Society of Chemistry, the journal is published in Semimonthly issues and has been indexed by SCIE, a leading international database. The journal focuses on the key research and cutting-edge progress in the field of chemistry-organic chemistry, publishes and reports the research results in this field in a timely manner, and is committed to becoming a window and platform for rapid academic exchanges among peers in this field. The journal's impact factor in 2023 is 2.9, and its CiteScore is 5.5.