Synthesis of Fused Imidazoles and Benzothiazoles from (Hetero)Aromatic ortho-Diamines or ortho-Aminothiophenol and Aldehydes Promoted by Chlorotrimethylsilane

Sergey V. Ryabukhin, Andrey S. Plaskon, Dmitriy M. Volochnyuk*, Andrey A. Tolmachev

*Institute of Organic Chemistry, National Academy of Sciences of Ukraine, Murmanska 5, Kyiv-94, 02094 Kiev, Ukraine, Email: D.Volochnyukenamine.net

S. V. Ryabukhin, A. S. Plaskon, D. M. Volochnyuk, A. A. Tolmachev, Synthesis, 2006, 3715-3726.

DOI: 10.1055/s-2006-950289

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Abstract

A set of benzimidazoles, 3H-imidazo[4,5-b]pyridines, purines, xanthines and benzothiazoles was readily prepared from (hetero)aromatic ortho-diamines or ortho-aminothiophenol and aldehydes using chlorotrimethylsilane in DMF as a promoter and water-acceptor agent, followed by oxidation with air oxygen.

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Key Words

Benzimidazoles, benzo-fused N-Heterocycles, Benzothiazoles, Oxygen, Aldehydes, Chlorotrimethylsilane, Parallel Synthesis, Sonochemistry

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ID: J66-Y2006-3710