Research on benz[c,d]indolin-2-one derivatives. Bromination of benz[c,d]indolin-2-onecarboxylic acids

It was experimentally observed that electrophilic substitution in, respectively, the 6 and 8 positions or the 8 position occurs when a carboxy group is present in the peri positions (in the 5 or 6 position) of benz[c,d]indolin-2-one. When two carboxy groups are simultaneously present in the 5 and 6 positions or when there is one carboxy group in the 6 position and a bromo substituent in the 5 position, the carboxy group is readily replaced by bromine. The electronic structures and reactivities of benz[c,d]indolin-2-one derivatives were investigated by spectroscopy and quantum chemistry.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 10, pp. 1363–1367, October, 1985.