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

Beilstein Journal of Organic Chemistry (Feb 2015)

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

Affiliations

A. V. Ivanov: 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; Fax: +7 3952 41-93-46
V. S. Shcherbakova: 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; Fax: +7 3952 41-93-46
I. A. Ushakov: 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; Fax: +7 3952 41-93-46
L. N. Sobenina: 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; Fax: +7 3952 41-93-46
O. V. Petrova: 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; Fax: +7 3952 41-93-46
A. I. Mikhaleva: 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; Fax: +7 3952 41-93-46
B. A. Trofimov: 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; Fax: +7 3952 41-93-46

DOI: https://doi.org/10.3762/bjoc.11.25
Journal volume & issue: Vol. 11, no. 1
pp. 228 – 232

Abstract

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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.

Published in Beilstein Journal of Organic Chemistry

ISSN: 1860-5397 (Online)
Publisher: Beilstein-Institut
Country of publisher: Germany
LCC subjects: Science: Chemistry: Organic chemistry
Website: http://www.beilstein-journals.org/bjoc

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