Synthesis, Characterization and in vitro Antibacterial evaluation of New Oxindoles and Spiro-Oxindoles Derivatives

Abstract

Arylidenes oxindole 3 and 5 were synthesized via the reactions of isatin 1 with malononitrile dimmer 2 and 5-amino-3-(cyanomethyl)-1H-pyrazole-4-carbonitrile 4. Compound 3 react by Michael addition with malononitrile, ethyl 2-cyanoacetate and acetyl acetone to give 6'-amino-2'-(dicyanomethylene)-2-oxo-2',3'-dihydro-1'H-spiro[indoline-3,4'-pyridine]-3',5'-dicarbonitrile 6a, 2'-(dicyanomethylene) 2,6'-dioxospiro[indoline-3,4'-piperidine]-3',5'-dicarbonitrile 6b and 2-(5'-acetyl-3'-cyano-6'-methyl-2-oxo-1'H-spiro[indoline-3,4'-pyridin]-2'(3'H) ylidene) malononitrile 7, respectively. compound 3 also, reacted with dimethylformamide dimethyl acetal to give N,N-dimethyl-N'-(1,1,3-tricyano-3-((Z)-2-oxoindolin-3-ylidene)prop-1-en-2-yl)formimidamide 7 which cyclized by ammonium acetate to give 4-amino-6-(cyano(2-oxoindolin-3-ylidene)methyl)pyrimidine-5-carbonitrile 8. Compound 5 reacted with dimedone 10 and acetyl acetone to give 3-(cyano(2-oxoindolin-3-ylidene)methyl)-5-((5,5-dimethyl-3-oxocyclohex-1-en-1-yl)amino)-1H-pyrazole-4-carbonitrile 11 and 2-(cyano(2-oxoindolin-3-ylidene)methyl)-5,7dimethylpyrazolo[1,5-a]pyrimidine-3-carbonitrile 12. Moreover, compound 3 and 5 reacted with hydrazine to give 3,3'-(hydrazine-1,2-diylidene)bis(indolin-2-one) 15. The antibacterial activities of the synthesized compounds were evaluated.