7-Acetylamino-, benzoylamino- and tosylamino-3-phenylisocarbostyril have been synthesized from the corresponding isocoumarins and aqueous ammonia. In an aqueous solution of methylamine, 7-acetylamino-3-phenylisocoumarin (2a) was hydrolyzed into 4'-acetylaminodesoxybenzoin-2'-carboxylic acid. 7-Acetylamino-N-methyl-3-phenylisocarbostyril was obtained by heating (2a) with methylamine in ethanol in an autoclave at 100°C for 10 hrs. Similarly, N-ethyl, N-n-propyl, and N-n-butyl analogs were prepared. N-Phenyl-isocarbostyril derivative was formed only when (2a) was treated with aniline in the presence of boric acid for 5 hrs at 200210°C. By heating a mixture of (2a) and o-phenylenediamine in the presence of polyphosphoric acid for 2 hrs at 200220°C, 2-amino-6-phenylbenzimidazo [2, 1-a] -isoquinoline (5) was formed. When boric acid was used as a condensing agent, N- (o-aminophenyl) -isocarbostyril derivative, instead of (5), was obtained. 6- Phenylbenzimidazo [2, 1-a] -isoquinoline and acetylamino derivative of (5) were also prepared. Infrared, ultraviolet absorption and fluorescence spectra of these new compounds were measured and discussed.
Four jointed compounds by formaldehyde [N-sulfomethylbenzamide (SMB), p-chloro-N-sulfomethylbenzamide (p-CSM), N-sulfomethyl-p-toluamide (SM-p-T) and N-sulfomethyl-p-anisamide (SM-p-A)] were synthesized, and their transjointing reactions investigated. Methylenebis-p-toluamide (MB-p-T), 4, 4'-dichloromethylenebisbenzamide (DCM) and diindolylmethane (DIM) were obtained by the reaction between SMB and each one of p-toluamide, p-chlorobenzamide and indole. Methylenebisbenzamide (MBB), DCM, MB-p-T, methylenebis-p-anisamide (MB-p-A), p-chloro-N-phthalimidomethylbenzamide, N-carbazolylmethyl-p-chlorobenzamide and DIM were obtained by the reaction between p-CSM and each one of benzamide, p-chlorobenzamide, p-toluamide, p-anisamide, phthalimide, carbazole, and indole. MBB, DCM, MB-p-T, MB-p-A, N-phthalimidomethyl-p-toluamide, N-carbazolylmethyl-p-toluamide and DIM were obtained by the reaction between SM-p-T and each one of benzamide, p-chlorobenzamide, p-toluamide, p-anisamide, phthalimide, carbazole and indole. Similarly, MBB, DCM, MB-p-T, MB-p-A, N-phthalimidomethyl-p-anisamide and DIM were obtained by the reaction between SM-p-A and each one of benzamide, p-chlorobenzamide, p-toluamide, p-anisamide, phthalimide and indole, respectively.