{"title":"烯胺类硫铵盐的重排和环化:取代吲哚的有效获取。","authors":"Zhixin Ren, Chengli Deng, Zi-Jing Bai, Wei Shi, Peng Gao","doi":"10.1021/acs.joc.5c00299","DOIUrl":null,"url":null,"abstract":"<p><p>A facile base-mediated cyclization and rearrangement of enamine thianthrenium salts for the construction of indole compounds is disclosed. In this reaction, sequential cleavage of two C-S bonds and subsequent formation of C-N and C-C bonds furnish a series of substituted indoles in moderate to good yields. Furthermore, an efficient late-stage functionalization of enamine compounds is established. The method features a wide substrate scope, good functional group tolerance, and low-cost starting materials.</p>","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":" ","pages":"7661-7672"},"PeriodicalIF":3.6000,"publicationDate":"2025-06-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Rearrangement and Cyclization of Enamine Thianthrenium Salts: Effective Access to Substituted Indoles.\",\"authors\":\"Zhixin Ren, Chengli Deng, Zi-Jing Bai, Wei Shi, Peng Gao\",\"doi\":\"10.1021/acs.joc.5c00299\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<p><p>A facile base-mediated cyclization and rearrangement of enamine thianthrenium salts for the construction of indole compounds is disclosed. In this reaction, sequential cleavage of two C-S bonds and subsequent formation of C-N and C-C bonds furnish a series of substituted indoles in moderate to good yields. Furthermore, an efficient late-stage functionalization of enamine compounds is established. The method features a wide substrate scope, good functional group tolerance, and low-cost starting materials.</p>\",\"PeriodicalId\":57,\"journal\":{\"name\":\"Journal of Organic Chemistry\",\"volume\":\" \",\"pages\":\"7661-7672\"},\"PeriodicalIF\":3.6000,\"publicationDate\":\"2025-06-13\",\"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.5c00299\",\"RegionNum\":2,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"2025/6/2 0:00:00\",\"PubModel\":\"Epub\",\"JCR\":\"Q1\",\"JCRName\":\"CHEMISTRY, ORGANIC\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Journal of Organic Chemistry","FirstCategoryId":"1","ListUrlMain":"https://doi.org/10.1021/acs.joc.5c00299","RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"2025/6/2 0:00:00","PubModel":"Epub","JCR":"Q1","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
Rearrangement and Cyclization of Enamine Thianthrenium Salts: Effective Access to Substituted Indoles.
A facile base-mediated cyclization and rearrangement of enamine thianthrenium salts for the construction of indole compounds is disclosed. In this reaction, sequential cleavage of two C-S bonds and subsequent formation of C-N and C-C bonds furnish a series of substituted indoles in moderate to good yields. Furthermore, an efficient late-stage functionalization of enamine compounds is established. The method features a wide substrate scope, good functional group tolerance, and low-cost starting materials.
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.