{"title":"Facile synthesis of benzo[e][1,2,4]triazepin-5-ones through a base medicated [4+3] cycloaddition","authors":"Eeda lingareddy , Ravindra M. Kumbhare","doi":"10.1016/j.tet.2025.134595","DOIUrl":null,"url":null,"abstract":"<div><div>Herein, we report the synthesis of highly functionalized benzo[e][1,2,4]triazepin-5-ones through a base medicated [4 + 3] cycloaddition of hydrazonoyl chloride and isatoic anhydride. The reaction proceeds through <em>in situ</em> generated nitrile imines from easily accessible hydrazonoyl chlorides. a simple organic base triethyl amine drives the reaction very successfully to give the desired products in excellent yields. The robustness of the [4 + 3] cycloaddition process is well evidented by broad substrate scope.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"179 ","pages":"Article 134595"},"PeriodicalIF":2.1000,"publicationDate":"2025-04-03","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/S0040402025001516","RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
Facile synthesis of benzo[e][1,2,4]triazepin-5-ones through a base medicated [4+3] cycloaddition
Herein, we report the synthesis of highly functionalized benzo[e][1,2,4]triazepin-5-ones through a base medicated [4 + 3] cycloaddition of hydrazonoyl chloride and isatoic anhydride. The reaction proceeds through in situ generated nitrile imines from easily accessible hydrazonoyl chlorides. a simple organic base triethyl amine drives the reaction very successfully to give the desired products in excellent yields. The robustness of the [4 + 3] cycloaddition process is well evidented by broad substrate scope.
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.