Premium
A novel synthesis of some 1,4‐phenylene‐bis‐heterocyclic carboxamide derivatives
Author(s) -
Abdelrazek Fathy M.,
Metwally Nadia H.,
Kassab Nazmi A.,
Sobhy Nehal A.
Publication year - 2009
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.257
Subject(s) - chemistry , carboxamide , piperidine , phenylene , medicinal chemistry , acrylamide , hydrazine (antidepressant) , reagent , ethanol , stereochemistry , organic chemistry , polymer , chromatography , copolymer
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).