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Synthesis 2009(21): 3603-3610  
DOI: 10.1055/s-0029-1216996
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

A Straightforward Synthesis of 2-(1-Vinyl-1H-pyrrol-2-yl)-1H-benzimidazoles from 1-Vinyl-1H-pyrrole-2-carbaldehydes and o-Phenylenediamine

Boris A. Trofimov*, Andrei V. Ivanov, Elena V. Skital’tseva, Alexander M. Vasil’tsov, Igor A. Ushakov, Konstantin B. Petrushenko, Al’bina I. Mikhaleva
A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, 1 Favorsky St., Irkutsk 664033, Russian Federation
Fax: +7(3952)419346; e-Mail: boris_trofimov@irioch.irk.ru;
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Publication History

Received 18 June 2009
Publication Date:
08 September 2009 (online)

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Abstract

Hitherto inaccessible 1-vinylpyrrole-benzimidazole ensembles have been synthesized by the condensation of 1-vinyl-1H-pyrrole-2-carbaldehydes with o-phenylenediamine either directly or via the intermediate Schiff bases of the 1-vinyl-1H-pyrrole-2-carbaldehydes (1% TFA, DMSO, air atmosphere, 60-70 ˚C, 1 h) in yields up to 89%, the intermediate Schiff bases of exclusively E configuration being isolated in 91-98% yield (1% TFA, DMSO, r.t., 30 min). The synthesized 2-(1-vinyl-1H-pyrrol-2-yl)-1H-benzimidazoles are intensely fluorescent, covering the practically important blue region (λmax 343-417 nm, Stokes shift 31-91 nm).

Key words

1-vinyl-1H-pyrrole-2-carbaldehydes - pyrrolylbenzimidazoles - o-phenylenediamine - Schiff bases - oxidative condensation

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