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Synthesis 2006(14): 2323-2326  
DOI: 10.1055/s-2006-942453
PAPER
© Georg Thieme Verlag Stuttgart · New York

Regioselective Annulation of Seven-, Eight-, and Nine-Membered Azaheterocycles to Benzimidazole Starting from Chloro-Substituted 2-Aza-1,3-dienes

Bogdan A. Demydchuka, Vladimir S. Brovaretsa, Alexander N. Chernegab, Eduard B. Rusanovb, Boris S. Drach*a
a Institute of Bioorganic Chemistry and Petrochemistry, National Academy of Sciences of Ukraine, Murmanskaya str. 1, 02094 Kiev, Ukraine
Fax: +380(44)5732561; e-Mail: drach@bpci.kiev.ua;
b Institute of Organic Chemistry, National Academy of Sciences of Ukraine, Murmanskaya str. 5, 02094 Kiev, Ukraine
Further Information

Publication History

Received 28 February 2006
Publication Date:
07 July 2006 (online)

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Abstract

Readily available 1-aryl-1,3,4,4-tetrachloro-2-azabuta-1,3-dienes enter into a pronouncedly directed cyclocondensation reaction with 2-(ω-aminoalkyl)benzimidazoles to give the corresponding seven-, eight-, and nine-membered azaheterocycles regioselectively annulated to the benzimidazole nucleus. The products thus obtained are derived from benzimidazole fused to 2H-1,3,5-triazepine, 1,3,5-triazocine, or 2H-1,3,5-triazonine, in accordance with comprehensive structural determination by spectroscopic methods and X-ray diffraction analysis.

Key words

2-(ω-aminoalkyl)benzimidazoles - 1,3,5-triazepine - 1,3,5-triazocine - 1,3,5-triazonine - regioselective annulation

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