{"title":"五氟吡啶 (PFPy) 介导的具有药用活性的 2,3-二氢喹唑啉-4(1H)-酮的一步法合成框架","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":"{\"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}","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
摘要
本文介绍了利用市售廉价五氟吡啶(PFPy)简单直接地一步合成 2,3-二氢喹唑啉-4(1H)-酮的方法。所报告的方案涉及 PFPy 介导的醛、胺和异酸酐在高温下的多组分缩合反应。这项研究工作利用了 PFPy 中氟原子的吸电子特性,在 N 原子的对位面上进行亲核取代,生成氟离子,从而帮助合成了 2,3-二氢喹唑啉-4(1H)-酮,收率极高。底物范围广、易于纯化、反应时间短、产率高和操作简便等特点增强了该方案的通用性。
Pentafluoropyridine (PFPy)-mediated one-pot framework for the synthesis of pharmaceutically active 2,3-dihydroquinazolin-4(1H)-ones
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.