Chemistry of Functionalized Benzazepines. 5 [1]. Synthesis and Chemical Transformation of the 1,2,4,5-Tetrahydrospiro- [3H-2-benzazepine-3,1′-cycloalkanes]

The synthesis of new spire derivatives of tetrahydro-2-benzazepine was accomplished and their nitration, bromination, allylation, acetylation, formylation and oxidation reactions were studied. Nitration and bromination of 5-methyl(1,5-dimethyl)-1,2,4,5-tetrahydrospiro[3H-2-benzazepine-3,1′- cycloalkane] took place regioselectively on position C-8 of the phenyl ring. A nitrone was obtained for the first time in the title series. The structures of the compounds were established by ir and nmr spectroscopy.