Abstract
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N,N′‐(1,4‐phenylene)bis(3‐oxo‐3‐phenylpropanamide) 1 reacts with DMFDMA in refluxing toluene to afford N,N′‐(1,4‐phenylene)bis(2‐benzoyl‐3‐(dimethylamino)acrylamide) 2. Compound 2 reacts with a twofold excess of the active methylene reagents 3a, 3b, 3c to afford the pent‐2‐enediamide derivatives 7 and 8a, 8b, respectively. Compounds 7 and 8a could be cyclized to afford the same compound N,N′‐(1,4‐phenylene)bis(5‐cyano‐6‐oxo‐2‐phenyl‐1,6‐dihydropyridine‐3‐carboxamide) 9a while 8b was cyclized to afford the 6‐thioxo analogue 9b. Compound 2 reacts with hydrazine derivatives 10a, 10b in refluxing ethanol/piperidine to afford the hydrazinylacrylamide derivatives 11a, 11b, which have been cyclized to the corresponding N,N′‐(1,4‐phenylene)bis(1__H__‐pyrazole‐4‐carboxamide) derivatives 12a, 12b, respectively. Compound 2 reacts also with urea derivatives 13a, 13b, 13c in refluxing ethanol/piperidine to afford the N,N′‐(1,4‐phenylene)bis(2‐benzoyl‐3‐substituted‐acrylamide) derivatives 14a‐c, which could be cyclized into N,N′‐(1,4‐phenylene)bis(6‐phenyl‐1,2‐dihydropyrimidine‐5‐carboxamide)‐2‐oxo; 2‐thioxo or 2‐imino derivatives 15a, 15b, 15c, respectively. J. Heterocyclic Chem., (2009).