Synthesis of 1H-isoindoliums by electrophile-mediated cascade cyclization/iodination of propargylamine-based 1, 6-diynes. Issue 18 (14th April 2022)

• Record Type: Journal Article
• Authors: Cui, Jian-Fang; Yu, Qiong; O, Wa-Yi; Huang, Li-Wu; Yang, Bin; Wong, Man-Kin
• Is Part Of: Organic & biomolecular chemistry. Volume 20:Issue 18(2022)
• Page Start: 3755
• Page End: 3762
• Publication Date: 2022-04-14
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/d2ob00316c
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : A highly regio- and chemoselective synthesis of 1 H -isoindoliums through a novel cascade cyclization reaction of propargylamine-based 1, 6-diynes has been developed. Abstract : A highly regio- and chemoselective synthesis of 1 H -isoindoliums through a facile and novel cascade cyclization reaction of propargylamine-based 1, 6-diynes under mild conditions has been developed. Different functional groups were compatible under the optimized reaction conditions, giving the corresponding products in up to 94% yields. Upon treatment with a base, the alkyne moiety of 1 H -isoindoliums could be further transformed to allenes in excellent yields.