Synthesis 2024; 56(15): 2347-2360
DOI: 10.1055/a-2282-7827
paper

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

Ludmila A. Oparina
,
Kseniya V. Belyaeva
,
Nikita A. Kolyvanov
,
Igor A. Ushakov
,
Elena F. Sagitova
,
Boris A. Trofimov
This work was financially supported by a grant from the Russian Science Foundation (project no. 21-73-10134).


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.

Supporting Information



Publication History

Received: 12 February 2024

Accepted after revision: 06 March 2024

Accepted Manuscript online:
06 March 2024

Article published online:
23 April 2024

© 2024. Thieme. All rights reserved

Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany

 
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