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Paper | Regular issue | Vol 29, No. 7, 1989, pp.1349-1354
Published online, 1st January, 1970
DOI: 10.3987/COM-89-4992
Reaction of o-Isocyanatobenzoyl Chloride with Cyanotrimethylsilane. Formation of 4-Oxo-4H-benzoxazine-2-carbonitrile and Its Ring Transformation to 3,4-Dihydro-1H-1,3,4-benzotriazepine-2,5-diones

Masahiko Takahashi* and Akira Hiratsuka

*Department of Materials Sciences, Faculty of Engineering, Ibaraki University, 4-12-1 Nakanarusawamachi, Hitachi, Ibaraki 316-8511, Japan


Reaction of O-isocyanatobenzoyl chloride (1) with cyanotrimethylsilane gave 4-oxo-4H-3,1-benzoxazine-2-carbonitrile (2), which was transformed to 3,4-dialkyl-3,4-dihydro-1H-1,3,4-benzotriazepine-2,5-diones (9) on treatment with 1,2-dialkylhydrazines. Halogenation of 9 gave 7-halotriazepines 10.