A cascade deprotonation/intramolecular aldol reaction of α-carbonyl sulfonium ylides with 2-mercaptoindole-3-carbaldehydes and 2-mercaptobenzaldehydes to access thieno[2, 3-b]indoles and benzothiophenes. Issue 16 (31st March 2021)

• Record Type: Journal Article
• Authors: Yang, Lei; Zhou, Shun; Zhao, Jian-Qiang; You, Yong; Wang, Zhen-Hua; Zhou, Ming-Qiang; Yuan, Wei-Cheng
• Is Part Of: Organic & biomolecular chemistry. Volume 19:Issue 16(2021)
• Page Start: 3678
• Page End: 3686
• Publication Date: 2021-03-31
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/d1ob00349f
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : An efficient cascade deprotonation/intramolecular aldol reaction of α -carbonyl sulfonium ylides with 2-mercaptoindole-3-carbaldehydes and 2-mercaptobenzaldehyde was developed for the synthesis of thieno[2, 3- b ]indoles and benzothiophenes. Abstract : The first catalyst-free cascade deprotonation/intramolecular aldol reaction of α-carbonyl sulfonium ylides with 2-mercaptoindole-3-carbaldehydes and 2-mercaptobenzaldehydes was developed. A series of thieno[2, 3- b ]indoles and benzothiophenes were smoothly obtained in high to excellent yields. The salient features of the protocol include catalyst-free conditions, an environment-friendly solvent, broad substrate scope, and large-scale synthesis.