Straightforward Approach to 5-Substituted 7H-Imidazo[2,1-b] [1,3]thiazines via Cyclization of 2-Alkynylthioimidazoles

Abstract

Electrophile-initiated nucleophilic cyclization of 2-alkynylthiobenzimidazoles is a useful tool for synthesizing new heterocyclic systems. However, halogen-initiated cyclization demonstrates poor selectivity between electrophilic addition and substitution reactions using other imidazole analogues. In this research, several different coinage metal catalysts were employed to broaden the scope of 7H-imidazo[2,1-b][1,3]thiazines in atom-economic manner. Selective 6-endo-dig pathway reactions were achieved in good to excellent yields using various 2-alkynylthioimidazoles with AuCl as the catalyst in DCE/DCM.

Key words

alkynes - 6-endo-dig cyclization - imidazoles - heterocycles - ring closure - gold catalysis

Publication History

Received: 10 July 2023

Accepted after revision: 20 September 2023

Accepted Manuscript online:
20 September 2023

Article published online:
23 October 2023

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