STUDIES ON BETA-KETOANILIDES - SYNTHESIS OF SOME NEW ISOQUINOLINE, PYRIMIDO[4,5-C]ISOQUINOLINE AND PHENANTHRIDINE DERIVATIVES

The beta-ketoanilides 1a,b or 2a,b react with the activated nitriles 3 a-c to give the isoquinoline derivatives 4a-e, respectively. The pyrim ido (4,5-c) isoquinoline derivatives 5a,b and 6a,b were obtained by th e reaction of 4a,b with carbon disulfide and/or formamide/formic acid. The phenanthridine derivatives 10 and 11 were produced by cyclization of 1a or 2a with PPA andlor POCl3 whereas the phenanthridine derivati ve 13 is obtained by the action of amm. acetate on 12 which is obtaine d from the reaction of 1a or 2a with m-cresol in the presence of PPA. The structures of the compounds have been confirmed by their IR, H-1 N MR and mass spectral data.