Functionalized 2,3'-Bipyrroles and Pyrrolo[1,2- c]imidazoles from Acylethynylpyrroles and Tosylmethylisocyanide

Maxim D Gotsko; Ivan V Saliy; Igor A Ushakov; Lyubov N Sobenina; Boris A Trofimov

doi:10.3390/molecules29040885

Functionalized 2,3'-Bipyrroles and Pyrrolo[1,2- c]imidazoles from Acylethynylpyrroles and Tosylmethylisocyanide

Molecules. 2024 Feb 17;29(4):885. doi: 10.3390/molecules29040885.

Authors

Maxim D Gotsko¹, Ivan V Saliy¹, Igor A Ushakov¹, Lyubov N Sobenina¹, Boris A Trofimov¹

Affiliation

¹ A.E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, 1 Favorsky Str., 664033 Irkutsk, Russia.

Abstract

An efficient method for the synthesis of pharmaceutically prospective but still rare functionalized 2,3'-bipyrroles (in up to 80% yield) by the cycloaddition of easily available acylethynylpyrroles with tosylmethylisocyanide (TosMIC) has been developed. The reaction proceeds under reflux (1 h) in the KOH/THF system. In the t-BuONa/THF system, TosMIC acts in two directions: along with 2,3'-bipyrroles, the unexpected formation of pyrrolo[1,2-c]imidazoles is also observed (products ratio~1:1).

Keywords: 2,3′-bipyrroles; acylethynylpyrroles; cycloaddition; pyrrolo[1,2-c]imidazoles; tosylmethylisocyanide.

Grants and funding

This research received no external funding.