Studies with enaminones: Synthesis of new cournarin-3-yl azoles, cournarin-3-yl azines, coumarin-3-yl azoloazines, coumarin-3-yl pyrone and coumarin-2-yl benzo[b]furans

3-Acetylcoumarine was condensed with dimethylformamide dimethylacetal (DMFD MA) to yield the enaminone, which reacts readily with hydroxylamine and wit h hydrazines to yield coumarin-3-ylisoxazoles and coumarin-3-ylpyrazoles re spectively. Reaction of the enaminone with benzamidine hydrochloride and 3- amino-1,2,4-1H-triazole affords the pyrimidine and triazolo[3,4-b]pyrimidin e. The enaminone reacts with hippuric acid and with the dithiocarboxylic ac id to yield pyranones. The reaction of the enaminone with 3-amino-1H-1,2,4- triazole gives the triazolo[3,4-b]pyrimidine. The enaminone underwent self dimerization on reflux in acetic acid ammonium acetate to yield the coumari nyl pyridines and reacted with ketone under the same conditions to yield th e pyridine. The reaction of the enaminone with 1,4-benzoquinone and 1,4-nap hthoquinone gives benzofuryl coumarine derivatives.