Stereoselective Synthesis of Acylethenyl Tetrahydropyridino- and Deazepanopyrrolo[1,2-c]imidazolidines via Annulation of Cyclic Imines with Acylethynylpyrroles

Abstract

A new and efficient strategy for the stereoselective synthesis of tetrahydropyridino- and deazepanopyrrolo[1,2-c]imidazolidines has been developed. Annulation of acylethynylpyrroles with six- and seven-membered cyclic imines (MeCN/THF, 20–25 °C, 24–72 h) leads to tetrahydropyrrolo[1′,2′:3,4]imidazo[1,2-a]pyridines and hexahydropyrrolo[1′,2′:3,4]imidazo[1,2-a]azepines with (E)-acylethenyl moiety in 28–96% yields.

Key words

acylethynylpyrroles - tetrahydropyridines - deazepanes - annulation - tetrahydropyrrolo[1′,2’:3,4]imidazo[1,2-a]pyridines - hexahydropyrrolo[1′,2′:3,4]imidazo[1,2-a]azepines

Publication History

Received: 12 February 2024

Accepted after revision: 06 March 2024

Accepted Manuscript online:
06 March 2024

Article published online:
23 April 2024

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