Experimental and theoretical studies on the functionalization reactions of 4-benzoyl-1,5-diphenyl-1H-pyrazole-3-carboxylic acid and acid chloride with 2,3-diaminopyridine.
The 1H-pyrazole-3-carboxylic acid 2 was converted in good yield (69%) into the corresponding 1H-pyrazole-3-carboxamide 5 via reaction of the acid chloride 3 with 2,3- diaminopyridine (4). A different product, the 3H-imidazo[4,5-b] pyridine derivative 6, was formed from the reaction of 3 with 4 and base in benzene for 5 hours. The structures of the synthesized compounds were determined spectroscopically. The mechanism of the reaction between 3 and 4 was examined theoretically.
Yildirim
Ismail
I
Department of Chemistry, Erciyes University, 38039, Kayseri, Turkey.
Kandemirli
Fatma
F
Demir
Elif
E
D000147:Acids, Heterocyclic / Q000138:chemical synthesis / Q000737:chemistry; D000631:Aminopyridines / Q000737:chemistry*; D001565:Benzoates / Q000737:chemistry; D002264:Carboxylic Acids / Q000737:chemistry*; D002626:Chemistry, Pharmaceutical; D002712:Chlorides / Q000737:chemistry*; D007700:Kinetics; D008958:Models, Molecular; D008968:Molecular Conformation; D011720:Pyrazoles / Q000737:chemistry*; D013816:Thermodynamics
D000147:Acids, Heterocyclic; D000631:Aminopyridines; D001565:Benzoates; D002264:Carboxylic Acids; D002712:Chlorides; D011720:Pyrazoles; C038615:2,3-diaminopyridine