Jingfeng Ye, Gengxin Li, Changfeng Wan, Jie-Ping Wan
{"title":"Chalcogen functionalized pyrimidine synthesis by three-component free radical chalcogenation and pyrimidine ring construction","authors":"Jingfeng Ye, Gengxin Li, Changfeng Wan, Jie-Ping Wan","doi":"10.1039/d5qo01206f","DOIUrl":null,"url":null,"abstract":"A rather facile transition metal-free protocol for the synthesis of chalcogen functionalized pyrimidines has been established via three-component reactions of enaminones, disulfides/diselenide, and amidines/guanidine. The reactions proceed efficiently in the presence of I2/KOH, and provides particularly practical and broadly applicable access to chalcogented pyrimidines. The reaction mechanism involving a key chalcogen (sulfur)-centered free radical has been verified by control experiments.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"57 1","pages":""},"PeriodicalIF":4.7000,"publicationDate":"2025-10-08","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Organic Chemistry Frontiers","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.1039/d5qo01206f","RegionNum":1,"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 rather facile transition metal-free protocol for the synthesis of chalcogen functionalized pyrimidines has been established via three-component reactions of enaminones, disulfides/diselenide, and amidines/guanidine. The reactions proceed efficiently in the presence of I2/KOH, and provides particularly practical and broadly applicable access to chalcogented pyrimidines. The reaction mechanism involving a key chalcogen (sulfur)-centered free radical has been verified by control experiments.
期刊介绍:
Organic Chemistry Frontiers is an esteemed journal that publishes high-quality research across the field of organic chemistry. It places a significant emphasis on studies that contribute substantially to the field by introducing new or significantly improved protocols and methodologies. The journal covers a wide array of topics which include, but are not limited to, organic synthesis, the development of synthetic methodologies, catalysis, natural products, functional organic materials, supramolecular and macromolecular chemistry, as well as physical and computational organic chemistry.