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Synfacts 2006(10): 0998-0998  
DOI: 10.1055/s-2006-949345
Synthesis of Heterocycles
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Benzimidazole-Fused Triazepines, Triazocines, and Triazonines

Contributor(s): Victor Snieckus, Todd Macklin
B. A. Demydchuk, V. S. Brovarets, A. N. Chernega, E. B. Rusanov, B. S. Drach*
National Academy of Sciences of Ukraine, Kiev, Ukraine
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Publication History

Publication Date:
21 September 2006 (online)

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Significance

The current report details the synthesis of several seven-, eight-, and nine-membered ring heterocycles by reaction of 2-(ω-amino­alkyl)benzimidazoles with tetrachloro-2-azabuta-1,3-dienes yielding benzimidazole-fused 1,3,5-triazepine, -triazocine, and -triazonine derivatives in excellent yields. The reaction occurs with complete regioselectivity, taking advantage of the higher electrophilicity of C-1 of the azadiene. X-ray crystal structures are given for two products.