Picolinic esters with hydroxybenzaldehydes and their imine derivatives

The reaction of hydroxybenzaldehydes with picolinic (2-pyridinecarboxylic) acid in the presence of DCC in dichloromethane afforded the corresponding esters in 77−88 % yield. By subsequent condensation of aldehydoesters with 4-aminoantipyrine in boiling methanol were synthesized their (E)-4-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1h-pyrazole4-il)imine in 65−75 % yield, but azomethines based on 2and 3-formylphenyl picolinates couldn’t be obtained due to alcoholysis of the ester groups. Quantum-chemical modeling of the electronic structure of the synthesized compounds using ab initio method with the HF/6-31G level of theory was performed for preliminary assessment of their potential antibacterial and antiviral properties.

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