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Synthesis 2003(8): 1272-1278
DOI: 10.1055/s-2003-39411
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

N- and C-Vinylation of Pyrroles with Disubstituted Activated Acetylenes

Boris A. Trofimov, Lyubov’ N. Sobenina*, Al’bina I. Mikhaleva, Igor A. Ushakov, Tamara I. Vakul’skaya, Zinaida V. Stepanova, Dar’ya-Syren D. Toryashinova, Anastasiya G. Mal’kina, Valentina N. Elokhina
A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, 1 Favorsky Street, Irkutsk 664033, Russia
Fax: +7(3952)396046; e-Mail: sobenina@irioch.irk.ru;
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Publication History

Received 3 March 2003
Publication Date:
26 May 2003 (online)

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Abstract

Addition of pyrrole and 2-phenylpyrrole to 2-acyl- and 2-cyano-1-phenylacetylenes in the KOH-DMSO system affords chemo- and regioselectively N-adducts: 1-(2-acyl- and 1-(2-cyano-1-phenylethenyl)pyrroles in 32-89% yield. 4,5,6,7-Tetrahydroindole reacts with 2-cyano-1-phenylacetylene analogously. Unexpectedly, with 2-benzoyl-1-phenylacetylene, the reaction follows mainly the C-vinylation route to give (E,Z)-2-(2-benzoyl-1-phenylethenyl)-4,5,6,7-tetrahydroindole and cyclo-bis-adduct, 2-(2-benzoyl-1,3-diphenyl-1,4,5,6,7,8-hexahydrocyclopenta[b]indol-1-yl)-1-phenylethanone, a product of intramolecular cyclization of 2,3-di(2-benzoyl-1-phenylethenyl)-4,5,6,7-tetrahydroindole.

Key words

pyrroles - alkynes - alkenation - chemoselectivity - regioselectivity - cyclizations - indoles

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