Construction of 4‐(Methylthio)isochromenones Skeleton through Regioselective Intramolecular Cyclization of 2‐Alkynylbenzoate Mediated by DMSO/[D6]DMSO and SOCl2. Issue 7 (6th February 2020)

• Record Type: Journal Article
• Authors: An, Xuechan; Zhang, Beibei; Li, Xiaoxian; Du, Tianshu; Ai, Zhenkang; Zhang, Chenglin; Xu, Jun; Sun, Fengxia; Zhang, Yilin; Du, Yunfei
• Is Part Of: European journal of organic chemistry. Issue 7(2020)
• Page Start: 852
• Page End: 859
• Publication Date: 2020-02-06
• Subjects: Alkynes -- Cyclization -- Oxygen heterocycles -- Synthetic methods; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201901723
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract : DMSO/SOCl2 was found to be an effective system for the intramolecular cyclization of 2‐alkynylbenzoates or 2‐alkynylbenzoic acids, which can afford biologically interesting 4‐(methylthio)isochromenones through regioselective electrophilic 6‐endo‐dig cyclization. DMSO plays the roles of both solvent and sulfur source and can also be replaced with its deuterated counterpart [D6 ]DMSO, enabling the incorporation of the SCD3 moiety into the isochromenone skeleton. Abstract : DMSO/SOCl2 was found to be an effective system for the intramolecular cyclization of 2‐alkynylbenzoates or 2‐alkynylbenzoic acids to afford biologically interesting 4‐(methylthio)isochromenones through a regioselective electrophilic 6‐endo‐dig cyclization. DMSO acts as both solvent and sulfur source and can also be replaced with its deuterated counterpart [D6 ]DMSO, enabling the incorporation of the SCD3 moiety.