Jiang Nan, Hanqing Zhang, Lanxin Zhu, Shilei Liu, Qiang Yan
{"title":"Divergent [5 + 1] Annulation of o-Aminobenzamides with Vinylene Carbonate as a Multifunctional Reagent","authors":"Jiang Nan, Hanqing Zhang, Lanxin Zhu, Shilei Liu, Qiang Yan","doi":"10.1021/acs.joc.5c00039","DOIUrl":null,"url":null,"abstract":"A divergent [5 + 1] cyclization reaction of <i>o</i>-aminobenzamides with vinylene carbonate has been developed, rapidly generating three types of cyclic molecules including quinazolinones, 2-methylquinazolinones, and 2,3-dihydroquinazolinones with high chemoselectivity. In this discovery, vinylene carbonate blooms as a multifunctional reagent to participate in cyclization. The potential of this new finding is further emphasized by assembling the benzothiazole heteroarene via the [4 + 1] version and tolerating bioactive units well.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"18 1","pages":""},"PeriodicalIF":3.6000,"publicationDate":"2025-04-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Journal of Organic Chemistry","FirstCategoryId":"1","ListUrlMain":"https://doi.org/10.1021/acs.joc.5c00039","RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
引用次数: 0
Abstract
A divergent [5 + 1] cyclization reaction of o-aminobenzamides with vinylene carbonate has been developed, rapidly generating three types of cyclic molecules including quinazolinones, 2-methylquinazolinones, and 2,3-dihydroquinazolinones with high chemoselectivity. In this discovery, vinylene carbonate blooms as a multifunctional reagent to participate in cyclization. The potential of this new finding is further emphasized by assembling the benzothiazole heteroarene via the [4 + 1] version and tolerating bioactive units well.
期刊介绍:
Journal of Organic Chemistry welcomes original contributions of fundamental research in all branches of the theory and practice of organic chemistry. In selecting manuscripts for publication, the editors place emphasis on the quality and novelty of the work, as well as the breadth of interest to the organic chemistry community.