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Communication | Regular issue | Vol 24, No. 4, 1986, pp.907-912
Published online, 1st January, 1970
DOI: 10.3987/R-1986-04-0907
Bridgehead Nitrogen Heterocycles. Synthesis of Methanoazepines Fused with Tetrazole, 1,2,4-Triazole and 1,2,4-Triazine

Shin-ichi Nagai, Naoki Kato, Taisei Ueda, Noriichi Oda, and Jinsaku Sakakibara*

*Faculty of Pharmaceutical Sciences, Nagoya City University, Tanabe-dori, Mizuho-ku, Nagoya 467-8603, Japan


Cyclohexa- (5a) and cycloheptatriazine (5b) were synthesized from the corresponding pyrazoles (3a-b). Hydrazinolysis of 2-ethoxy-3-azabicyclo[3.2.1]octan-2-ene (7c) gave 2-hydrazino-3-azabicyclo[3.2.1]octan-2-ene (7d) which readily underwent ring closure with nitrous acid, triethyl orthoformate and ethyl pyruvate to afford tetrazolo[1,5-a]azepine (8), 1,2,4-triazolo[4,3-a]azepine (9) and 1,2,4-triazino[4,3-a]azepine (10).