Interaction of tetracyanoethylene (TCE) with active methylene compounds: synthesis, reactions and spectral characterization of some novel 2-pyrazoline-5-one compounds. Computational studies on the synthesized molecules by DFT

Abstract

Tetracyanoethylene(TCE) (6 ) was reacted with 3-methyl-1-(3-bromophenyl)-2-pyrazolin-5one (7) to give 1-(3-bomophenyl)-4-dicyanomethylene-3-methyl-2-pyrazolin-5-one (8). Also, TCE compound 6 was reacted with diethyl malonate, malonic acid dihydrazide, and ethyl acetoacetate and ethyl cyanoacetate to afford carbon acids 10a-d, respectively. Compound 8 was heated at reflux with aniline to give compound 13. Compound 8 was treated with N, Ndimethyl aniline to give the very stable violet compound 15. Also compound 8 was refluxed with glycine to yield the pyrazolone derivative 16 which reacted with N-phenyl malimide to give the adduct 17. The molecular structure of 1-(3-bromophenyl 4-dicyanomethylene-3methyl-2-pyrazolin-5-one molecule 8 in the ground state was computed by density functional theory (DFT) using 6-311G basis set and B3LYP level of theory.