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Communication | Regular issue | Vol 3, No. 1, 1975, pp.15-18
Published online, 1st January, 1970
DOI: 10.3987/R-1975-01-0015
Studies on Medium-membered Heterocyclic Compounds. I. The Formation of 2,5-Diphenyl-3,4-diaza-2,4-norcaradiene from 4,6-Dihydro-3,7-diphenyl-1,2-diazepine

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 4,6-dihydro-3,7-diphenyl-1,2-diazepine (2) with NBS or bromine afforded 4-methyl-3,6-diphenylpyridazine (3) which is formed from 2,5-diphenyl-3,4-diaza-2,4-norcaradiene (1) and hydrogen bromide. The dihydrodiazepine 2, reacted with chlorine or sulfuryl chloride, giving 1 and 4,5,5,6-tetrachloro- 4,6-dihydro-3,7-diphenyl-1,2-diazepine (4).