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Synthesis 2010(22): 3913-3917  
DOI: 10.1055/s-0030-1258249
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Efficient One-Pot Synthesis of Spirooxindole Derivatives Containing 1,4-Dihydropyridine-Fused-1,3-Diazaheterocycle Fragments via Four-Component Reaction

Abdolali Alizadeh*, Tahereh Firuzyar, Azadeh Mikaeili
Department of Chemistry, Tarbiat Modares University, P.O. Box 14115-175, Tehran, Iran
Fax: +98(21)88006544; e-Mail: abdol_alizad@yahoo.com; e-Mail: aalizadeh@modares.ac.ir;
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Publication History

Received 16 July 2010
Publication Date:
14 September 2010 (online)

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Abstract

An efficient, one-pot synthetic protocol toward spirooxindole derivatives containing 1,4-dihydropyridine-fused 1,3-diazaheterocycle fragments, a class of biologically active compounds starting from 1,1-bis(methylthio)-2-nitroethylene, 1,n-diamine, isatin, or its derivatives, and malononitrile is described. The reaction proceeds in ethanol in the presence of 10 mol% of piperidine as a basic catalyst under reflux conditions to produce the title compounds in 74-85% yields.

Key words

spirooxindole - 1,4-dihydropyridine - malononitrile - 1,n-diamine - 1,1-bis(methylthio)-2-nitroethylene - multicomponent reaction

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