2-(1-Hydroxypropyn-2-yl)-1-vinylpyrroles: the first successful Favorsky ethynylation of pyrrolecarbaldehydes

A V Ivanov; V S Shcherbakova; I A Ushakov; L N Sobenina; O V Petrova; A I Mikhaleva; B A Trofimov

doi:10.3762/bjoc.11.25

2-(1-Hydroxypropyn-2-yl)-1-vinylpyrroles: the first successful Favorsky ethynylation of pyrrolecarbaldehydes

Beilstein J Org Chem. 2015 Feb 10:11:228-32. doi: 10.3762/bjoc.11.25. eCollection 2015.

Authors

A V Ivanov¹, V S Shcherbakova¹, I A Ushakov¹, L N Sobenina¹, O V Petrova¹, A I Mikhaleva¹, B A Trofimov¹

Affiliation

¹ A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, 1 Favorsky Str., Irkutsk 664033, Russia, Tel: +7 3952 42-56-31;

Abstract

1-Vinylpyrrole-2-carbaldehydes react with acetylene at atmospheric pressure in a NaOH/EtOH/DMSO system at 7-10 °C to afford 2-(1-hydroxypropyn-2-yl)-1-vinylpyrroles in 53-94% yield. Thus, the first base-mediated direct ethynylation of pyrrolecarbaldehydes with free acetylene under modified conditions of the Favorsky reaction has been implemented to pave an expedient route to important biomolecules containing a pyrrole ring.

Keywords: 1-vinylpyrrole-2-carbaldehyde; Favorsky reaction; acetylene; ethynylation.