{"title":"Fe-Catalyzed Hydrocyclization of Inactivated Alkenes to Synthesize Ring-Fused 2,3-Dihydroquinazolinone","authors":"Youlu Pan, Chaonan Tang, Xianming Zeng, Yingchen Zhu, Wenhai Huang, Wenting Du","doi":"10.1021/acs.joc.4c02410","DOIUrl":null,"url":null,"abstract":"A Fe-catalyzed hydrocyclization reaction of unactivated alkenes was developed, utilizing PhSiH<sub>3</sub> as the hydrogen source, yielding 2,3-dihydroquinazolinone (DHQZ) derivatives in moderate to good yields. Notably, when the substrate was switched to <i>N</i>-cyano-<i>N</i>-(2-(prop-1-en-2-yl)phenyl)benzamides, the reaction yielded only the unreduced products. Mechanistic studies revealed that the intramolecular addition of the in situ formed radical to the unactivated alkene results in the formation of the fused ring.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"7 1","pages":""},"PeriodicalIF":3.3000,"publicationDate":"2025-01-22","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.4c02410","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 Fe-catalyzed hydrocyclization reaction of unactivated alkenes was developed, utilizing PhSiH3 as the hydrogen source, yielding 2,3-dihydroquinazolinone (DHQZ) derivatives in moderate to good yields. Notably, when the substrate was switched to N-cyano-N-(2-(prop-1-en-2-yl)phenyl)benzamides, the reaction yielded only the unreduced products. Mechanistic studies revealed that the intramolecular addition of the in situ formed radical to the unactivated alkene results in the formation of the fused ring.
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.