Bin Qiu , Ya-Fei Shi , Xiao-De An , Shu-Kui Guo , Yao-Bin Shen , Jian Xiao
{"title":"基于直接构造菲的新型萘融合2-氨基吲哚和萘醌的发散合成","authors":"Bin Qiu , Ya-Fei Shi , Xiao-De An , Shu-Kui Guo , Yao-Bin Shen , Jian Xiao","doi":"10.1016/j.gresc.2023.11.001","DOIUrl":null,"url":null,"abstract":"<div><div>An environmentally friendly, highly atom-economical and operationally simple approach toward the synthesis of naphtho-fused 2-aminoindolines and naphthoxindoles starting from biaryl aldehydes and secondary amines has been developed. This notable methodology integrates consecutive intramolecular Mannich-type cyclization triggered by the dearomatization of indole with subsequent aromatization <em>via β</em>-elimination and then amination or oxidation at the C2-position of the indole nucleus. The secondary amine-controlled divergent protocol together with an easy product isolation process provides a practical route for the first time to access naphtho-fused 2-substituted indoline.</div></div>","PeriodicalId":12794,"journal":{"name":"Green Synthesis and Catalysis","volume":"6 1","pages":"Pages 110-113"},"PeriodicalIF":0.0000,"publicationDate":"2025-02-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Divergent synthesis of new naphtho-fused 2-aminoindolines and naphthoxindoles based on straightforward construction of phenanthrene\",\"authors\":\"Bin Qiu , Ya-Fei Shi , Xiao-De An , Shu-Kui Guo , Yao-Bin Shen , Jian Xiao\",\"doi\":\"10.1016/j.gresc.2023.11.001\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div><div>An environmentally friendly, highly atom-economical and operationally simple approach toward the synthesis of naphtho-fused 2-aminoindolines and naphthoxindoles starting from biaryl aldehydes and secondary amines has been developed. This notable methodology integrates consecutive intramolecular Mannich-type cyclization triggered by the dearomatization of indole with subsequent aromatization <em>via β</em>-elimination and then amination or oxidation at the C2-position of the indole nucleus. The secondary amine-controlled divergent protocol together with an easy product isolation process provides a practical route for the first time to access naphtho-fused 2-substituted indoline.</div></div>\",\"PeriodicalId\":12794,\"journal\":{\"name\":\"Green Synthesis and Catalysis\",\"volume\":\"6 1\",\"pages\":\"Pages 110-113\"},\"PeriodicalIF\":0.0000,\"publicationDate\":\"2025-02-01\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Green Synthesis and Catalysis\",\"FirstCategoryId\":\"1085\",\"ListUrlMain\":\"https://www.sciencedirect.com/science/article/pii/S2666554923000832\",\"RegionNum\":0,\"RegionCategory\":null,\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"\",\"JCRName\":\"\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Green Synthesis and Catalysis","FirstCategoryId":"1085","ListUrlMain":"https://www.sciencedirect.com/science/article/pii/S2666554923000832","RegionNum":0,"RegionCategory":null,"ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"","JCRName":"","Score":null,"Total":0}
Divergent synthesis of new naphtho-fused 2-aminoindolines and naphthoxindoles based on straightforward construction of phenanthrene
An environmentally friendly, highly atom-economical and operationally simple approach toward the synthesis of naphtho-fused 2-aminoindolines and naphthoxindoles starting from biaryl aldehydes and secondary amines has been developed. This notable methodology integrates consecutive intramolecular Mannich-type cyclization triggered by the dearomatization of indole with subsequent aromatization via β-elimination and then amination or oxidation at the C2-position of the indole nucleus. The secondary amine-controlled divergent protocol together with an easy product isolation process provides a practical route for the first time to access naphtho-fused 2-substituted indoline.