{"title":"Pentafluoropyridine (PFPy)-mediated one-pot framework for the synthesis of pharmaceutically active 2,3-dihydroquinazolin-4(1H)-ones","authors":"Ashish Kumar , Shashi Pandey , Monika Gupta , Chatrasal S. Rajput","doi":"10.1016/j.tet.2024.134248","DOIUrl":null,"url":null,"abstract":"<div><p>This article describes the employment of commercially available, cheap pentafluoropyridine (PFPy) for a simple and straightforward one-pot synthesis of 2, 3-Dihydroquinazolin-4(1<em>H</em>)-ones. The reported protocol involves PFPy-mediated multicomponent condensation reaction of aldehyde, amine and isatoic anhydride at elevated temperature. This research work exploited the electron-withdrawing nature of fluorine atoms in PFPy for the nucleophilic substitution at <em>para</em> to the <em>N</em>-atom to produce fluoride ions that assisted the synthesis of the 2,3-Dihydroquinazolin-4(<em>1H</em>)-ones in excellent yield. The broad substrate scope, easy purification, short reaction times, high yields and ease of operation enhance the versatility of the protocol.</p></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":null,"pages":null},"PeriodicalIF":2.1000,"publicationDate":"2024-09-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Tetrahedron","FirstCategoryId":"92","ListUrlMain":"https://www.sciencedirect.com/science/article/pii/S0040402024004289","RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
引用次数: 0
Abstract
This article describes the employment of commercially available, cheap pentafluoropyridine (PFPy) for a simple and straightforward one-pot synthesis of 2, 3-Dihydroquinazolin-4(1H)-ones. The reported protocol involves PFPy-mediated multicomponent condensation reaction of aldehyde, amine and isatoic anhydride at elevated temperature. This research work exploited the electron-withdrawing nature of fluorine atoms in PFPy for the nucleophilic substitution at para to the N-atom to produce fluoride ions that assisted the synthesis of the 2,3-Dihydroquinazolin-4(1H)-ones in excellent yield. The broad substrate scope, easy purification, short reaction times, high yields and ease of operation enhance the versatility of the protocol.
期刊介绍:
Tetrahedron publishes full accounts of research having outstanding significance in the broad field of organic chemistry and its related disciplines, such as organic materials and bio-organic chemistry.
Regular papers in Tetrahedron are expected to represent detailed accounts of an original study having substantially greater scope and details than that found in a communication, as published in Tetrahedron Letters.
Tetrahedron also publishes thematic collections of papers as special issues and ''Reports'', commissioned in-depth reviews providing a comprehensive overview of a research area.