Experimental and quantum-chemical calculations on some 1H-pyrazole-3-carboxamide and-3-carboxylate derivatives formation

Yildirim I., Kandemirli F., Akcamur Y.

JOURNAL OF MOLECULAR STRUCTURE, vol.738, pp.275-279, 2005 (SCI-Expanded) identifier identifier


The 1H-pyrazole-3-carboxylic acid was converted via reactions of its acid chloride 1 with various binucleophiles like 1,2-diaminoethane (2a), 1,2-diaminopropane (2b) and 2-amino-2-methylpropanol (2c) into the corresponding 1H-pyrazole-3-carboxamides and -3-carboxylate 3a-c, respectively, in good yields (66-95%). The reactions of 1 with aliphatic diamines and amino alcohols (2a-c) in benzene for 5-6 h with catalytic amounts of pyridine lead to the products 3a-c formation. The structures of these new synthesized compounds were determined from the C-13 NMR, H-1 NMR, IR spectroscopic data and elemental analyses. All of them were compared with their previous analogs. The mechanism of reaction between 1 and 2a-c was studied by means of semi-empirical AM1 calculations. (c) 2005 Elsevier B.V. All rights reserved.