Reactivity of 2,3-Pyridine Dicarboxylic Anhydride Towards some Nitrogen Nucleophilic Reagents: Synthesis and Antimicrobial Evaluation of some Pyridine Carboxamide and Pyrrolo[3,4-B]Pyridine-5,7-Dione Derivatives
The reactivity of 2,3-pyridine dicarboxylic anhydride towards some nitrogen nucleophiles under different conditions was studied. Thus, the reaction of anhydride with substituted anilines (X = 3-COOH, 4-COOH, 4-COOC2H5, 2-OC2H5, 4-OC2H5) in acetic acid at room temperature or toluene under reflux afforded arylcarbamoylpyridinecarboxylic acid. Repeating the same reaction under heating gave rise to a mixture of cyclic imide and nicotinamides. On the other hand, treatment of anhydride with binucleophiles (1,4-phenylenediamine, benzidine, 4,4`-diaminodiphenyl-sulfone) in glacial acetic acid at room temperature (or toluene under reflux) afforded pyrrolopyridine derivatives rather than carboxamide derivatives. The reaction of anhydride with binucleophiles in acetic acid under reflux afforded nicotinamide derivatives. Antimicrobial activities of some selected compounds were screened.