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Synthesis 2011(17): 2843-2847  
DOI: 10.1055/s-0030-1260134
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of 1-Vinylpyrrole-imidazole Alkaloids

Kseniya V. Belyaeva, Ludmila V. Andriyankova, Lina P. Nikitina, Andrei V. Ivanov, Andrei V. Afonin, Igor’ A. Ushakov, Anastasiya G. Mal’kina, Al’bina I. Mikhaleva, Boris A. Trofimov*
A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, 1 Favorsky Str., 664033 Irkutsk, Russian Federation
Fax: +7(3952)419346; e-Mail: boris_trofimov@irioch.irk.ru;
Further Information

Publication History

Received 2 June 2011
Publication Date:
25 July 2011 (online)

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Abstract

The reaction between 1-methylimidazole, cyano(phen­yl)acetylene, and 1-vinylpyrrole-2-carbaldehydes (MeCN, 20-25 ˚C) stereoselectively gives 1-vinylpyrrole-imidazole ensembles with a (Z,Z)-bis(2-cyano-1-phenylvinyl)oxy function in up to 45% yield. Unlike recently reported three-component reaction between imidazoles, electron-deficient acetylenes, and aldehydes affording 1:1:1 adducts, in this case two molecules of acetylene are involved to deliver 1:2:1 adducts thus representing a novel functionalizaton of the pyrrole-imidazole alkaloid scaffold. The initial zwitterion generated from imidazole and cyano(phenyl)acetylene is thought to be transformed into a carbene, which reacts with pyrrole-2-carbaldehyde. Two subsequent rearrangements of the 1:1:1 adduct furnish the intermediate pyrrole-imidazole ensemble, which in its enol form adds to second molecule of cyano(phenyl)acetylene to yield the final products, functionalized pyrrole-imidazole alkaloids.

Key words

1-methylimidazole - cyano(phenyl)acetylene - 1-vinyl­pyrrole-2-carbaldehydes - three-component reaction - pyrrole-imidazole alkaloids

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