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Synthesis 2010(9): 1536-1542  
DOI: 10.1055/s-0029-1218704
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Exceptionally Easy Ring Cleavage of Benzimidazoles by α,β-Acetylenic γ-Hydroxy Nitriles and Water

Boris A. Trofimov*, Ludmila V. Andriyankova, Lina P. Nikitina, Kseniya V. Belyaeva, Anastasiya G. Mal’kina, Andrei V. Afonin
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;
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Publikationsverlauf

Received 27 January 2010
Publikationsdatum:
15. März 2010 (online)

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Abstract

The three-component reaction of a benzimidazole with an α,β-acetylenic γ-hydroxy nitrile and water in acetonitrile at 20-25 ˚C for seven days or at 45-50 ˚C for six hours results in cleavage of the imidazole ring to afford the corresponding (2-{[(3E)-5-aminofuran-3(2H)-ylidene]amino}phenyl)formamide exclusively in 84-99% yield. The synthesis involves multipositional cascade transformations of the intermediate hemiaminals formed from the primary zwitterions and water.

Key words

alkynes - benzimidazoles - heterocycles - multicomponent reactions - nitriles - ring opening - polycycles

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