European Journal of Chemistry

Tetra-n-butylammonium fluoride-mediated dimerization of (α-methylbenzylidene)malononitriles to form polyfunctional 5,6-dihydropyridines derivatives under solvent-free conditions



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Abdul Hameed
Ayaz Anwar
Sammer Yousaf
Khalid Mohammed Khan
Fatima Zahra Basha

Abstract

A series of polyfunctional dihydropyridine 28-46 were prepared via dimerization of readily available substituted (a-methylbenzylidene)-malononitriles 10-27 by treating with neat TBAF.3H2O under solvent-free conditions at 85-90 oC. All the dimers 28-46 were obtained in high yield from their corresponding substituted alkylidenemalononitriles except in the case of 2-chloro (15), 2-hydroxy (21), and 2-nitro (26) substituted alkylidenemalononitriles where the reaction was unsuccessful due to the steric interaction between methylene group and the substituents present at ortho position. The X-ray crystallographic studies of compounds 28 and 30 were carried out to confirm the structure of dimerized product. The method is eco-friendly and wider is scope to prepare a range of substituted dihydropyridine derivatives 28-46.

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Hameed, A.; Anwar, A.; Yousaf, S.; Khan, K. M.; Basha, F. Z. Tetra-N-Butylammonium Fluoride-Mediated Dimerization of (α-methylbenzylidene)malononitriles to Form Polyfunctional 5,6-Dihydropyridines Derivatives under Solvent-Free Conditions. Eur. J. Chem. 2012, 3, 179-185.

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