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Communication | Regular issue | Vol 3, No. 7, 1975, pp.547-552
Published online, 1st January, 1970
DOI: 10.3987/R-1975-07-0547
Studies of Medium-membered Heterocyclic Compounds. II. Reaction of 5-Benzyl-4,6-dihydro-3,7-diaryl-1,2,5-triazepines with Halogenation-reagents

Otohiko Tsuge* and Kichinosuke Kamata

*Research Institute of Industrial Science, Faculty of Engineering, Kyushu University, 6-1, Kasuga-koen, Kasuga 816-8580, Japan


Treatment of 5-benzyl-4,6-dihydro-3,7-diaryl-1,2,5-triazepine (6a or 6b) with bromination-reagents afforded either 1-benzyl-4-arylimidazole (7a or 7b) or 3,6-diarylpyridazine (2a or 2b) as the main product, depending on the reaction conditions. On the other hand, 6a reacted with sulfuryl chloride to give 4-benzylamino-3,6-diphenylpyridazine (8), while the reaction of 6 with chlorine gas afforded 5-chloropyridazine derivative (9), which was easily obtained by further chlorination of 8. Although the reaction course for the formation of 2 is not clear, the products 7 and 8 can be accounted for by the pathway via triazanorcaradiene (10).