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

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

Abstract New convenient conditions for benzimidazole and benzothiazole syntheses are described. 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 chlorotrim...

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Veröffentlicht in:Synthesis (Stuttgart) 2006-11, Vol.2006 (21), p.3715-3726
Hauptverfasser: Ryabukhin, Sergey V., Plaskon, Andrey S., Volochnyuk, Dmitriy M., Tolmachev, Andrey A.
Format: Artikel
Sprache:eng
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Zusammenfassung:Abstract New convenient conditions for benzimidazole and benzothiazole syntheses are described. 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.
ISSN:0039-7881
1437-210X
DOI:10.1055/s-2006-950289