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Communication | Regular issue | Vol 20, No. 11, 1983, pp.2173-2176
Published online, 1st January, 1970
DOI: 10.3987/R-1983-11-2173
Synthesis of the First Examples of N-Unsubstituted 1,3-Benzodiazepines

Jyoji Kurita, Michiko Enkaku, and Takashi Tsuchiya

*School of Pharmacy, Hokuriku University, 3-Ho, Kanagawa machi, Kanazawa 920-1181, Japan

Abstract

Treatment of both 3-benzyloxycarbonyl-3H-1,3- (6) and 1-benzyloxycarbonyl-1H-1,3-benzodiazepine (9) with trimethylsilyl iodide resulted in decarboxylation to give the N-unsubstituted 3H-1,3-benzodiazepine hydroiodide (8), which, on treatment with base, yielded the free bases (11). The 1,3-thienodiazepines (14) and (15) gave similar results. These results may indicate that the 3H-tautomers are most stable in the possible three 1,3-benzodiazepine tautomers.