Abstract

Synthesis of novel mannich bases containing pyrazolones and indole systems

Author(s): P.Nagarjuna Reddy, L.K.Ravindranath, K.B.Chandrasekhar, P.Rameshbabu,G.Madhu, K.S.Bhavani Aiswarya

Novel mannich bases N-(2- ((R) -1- ((Z) -2- (1-((4-methyl piperazin-1-yl) methyl) -2-oxoindolin-3-ylidene) hydrazinyl) -1-oxopropan -2-ylamino) -2-oxoethyl) -4-(5–oxo –4-(2-phenyl hydrazono) -3-(trifluoromethyl) -4, 5- dihydro -1H –pyrazol -1-yl) benzamide were synthesized by the condensation reaction between (R)-N-(2-(1- hydrazinyl-1-oxopropan-2-ylamino)-2-oxoethyl)-4-(5–oxo–4-(2-phenyl hydrazono)-3- (trifluoromethyl) -4, 5- dihydro -1H –pyrazol -1 -yl) benzamide with isatin afford corresponding N-(2-oxo-2-((R)-1-oxo-1-((Z)-2-(2- oxoindolin-3-ylidene)hydrazinyl)propan-2-ylamino)ethyl)-4-(5–oxo–4-(2-phenylhydrazono)-3-(trifluoromethyl)-4, 5-dihydro-1H-pyrazol-1-yl)benzamide.This was subjected to mannich reaction with cyclic secondary amine such as piperidine/marpholine/N-methyl piperidine in the presence of formaldehyde in DMF to give corresponding mannich base N-(2- ((R) -1- ((Z) -2- (1-((4-methyl piperazin-1-yl) methyl) -2-oxoindolin-3-ylidene) hydrazinyl) -1-oxopropan -2-ylamino) -2-oxoethyl) -4-(5–oxo –4-(2-phenyl hydrazono) -3-(trifluoromethyl) -4, 5-dihydro -1H –pyrazol -1-yl) benzamide in excellent yields.The structure of these newly synthesized compounds were characterized by 1HNMR, Mass, IR&Elemental analysis.

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