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

Autor: Ivanov AV; 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;, Shcherbakova VS; 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;, Ushakov IA; 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;, Sobenina LN; 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;, Petrova OV; 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;, Mikhaleva AI; 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;, Trofimov BA; 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;
Jazyk: angličtina
Zdroj: Beilstein journal of organic chemistry [Beilstein J Org Chem] 2015 Feb 10; Vol. 11, pp. 228-32. Date of Electronic Publication: 2015 Feb 10 (Print Publication: 2015).
DOI: 10.3762/bjoc.11.25
Abstrakt: 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.
Databáze: MEDLINE
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