{"title":"Iron-Mediated Bromocyclization of Olefinic Amides for the Synthesis of Bromobenzoxazines","authors":"Da‐Zhen Xu, Tong-Tong Zhao, Qiang Bian, Yu-Wei Zhao, Lin-Lin Xu, Wei-Guang Zhao","doi":"10.1055/a-2338-8479","DOIUrl":null,"url":null,"abstract":"An iron-mediated bromination/cyclization for the synthesis of bromobenzoxazines from olefinic amides has been successfully developed. In this protocol, the simple iron salt FeBr3 was employed as a bromination reagent, giving the bromobenzoxazine products in moderate to excellent yields. This methodology features good functional group tolerance, gram-scale synthesis and green reaction conditions by the use of air as the terminal oxidant. Preliminary mechanistic studies suggest that a free radical pathway is involved.","PeriodicalId":501298,"journal":{"name":"Synthesis","volume":"36 9","pages":""},"PeriodicalIF":0.0000,"publicationDate":"2024-06-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Synthesis","FirstCategoryId":"1085","ListUrlMain":"https://doi.org/10.1055/a-2338-8479","RegionNum":0,"RegionCategory":null,"ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"","JCRName":"","Score":null,"Total":0}
引用次数: 0
Abstract
An iron-mediated bromination/cyclization for the synthesis of bromobenzoxazines from olefinic amides has been successfully developed. In this protocol, the simple iron salt FeBr3 was employed as a bromination reagent, giving the bromobenzoxazine products in moderate to excellent yields. This methodology features good functional group tolerance, gram-scale synthesis and green reaction conditions by the use of air as the terminal oxidant. Preliminary mechanistic studies suggest that a free radical pathway is involved.
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