Catalyst-Free Annulation of Acylethynylpyrroles with 1-Pyrrolines: A Straightforward Access to Tetrahydrodipyrrolo[1,2- a:1',2'- c]imidazoles

Ludmila A Oparina; Kseniya V Belyaeva; Nikita A Kolyvanov; Igor A Ushakov; Maxim D Gotsko; Lyubov' N Sobenina; Alexander V Vashchenko; Boris A Trofimov

doi:10.1021/acs.joc.2c00476

Catalyst-Free Annulation of Acylethynylpyrroles with 1-Pyrrolines: A Straightforward Access to Tetrahydrodipyrrolo[1,2- a:1',2'- c]imidazoles

J Org Chem. 2022 Aug 5;87(15):9518-9531. doi: 10.1021/acs.joc.2c00476. Epub 2022 Jul 18.

Authors

Ludmila A Oparina¹, Kseniya V Belyaeva¹, Nikita A Kolyvanov¹, Igor A Ushakov¹, Maxim D Gotsko¹, Lyubov' N Sobenina¹, Alexander V Vashchenko¹, Boris A Trofimov¹

Affiliation

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

PMID: 35849567
DOI: 10.1021/acs.joc.2c00476

Abstract

Acylethynylpyrroles undergo facile (rt, MeCN or MeOH, 24-72 h) catalyst-free annulation with 1-pyrrolines to afford acylmethylenetetrahydrodipyrrolo[1,2-a:1',2'-c]imidazoles in up to 93% yield and 90% E-stereoselectivity of the olefin moiety.