European Journal of Chemistry 2012, 3(2), 179-185. doi:10.5155/eurjchem.3.2.179-185.562

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


Abdul Hameed (1,*) , Ayaz Anwar (2) , Sammer Yousaf (3) , Khalid Mohammed Khan (4) , Fatima Zahra Basha (5)

(1) Husein Ebrahim Jamal Research Institute of Chemistry, International Center for Chemical and Biological Sciences, University of Karachi, Karachi, 75270, Pakistan
(2) Husein Ebrahim Jamal Research Institute of Chemistry, International Center for Chemical and Biological Sciences, University of Karachi, Karachi, 75270, Pakistan
(3) Husein Ebrahim Jamal Research Institute of Chemistry, International Center for Chemical and Biological Sciences, University of Karachi, Karachi, 75270, Pakistan
(4) Husein Ebrahim Jamal Research Institute of Chemistry, International Center for Chemical and Biological Sciences, University of Karachi, Karachi, 75270, Pakistan
(5) Husein Ebrahim Jamal Research Institute of Chemistry, International Center for Chemical and Biological Sciences, University of Karachi, Karachi, 75270, Pakistan
(*) Corresponding Author

Received: 25 Nov 2011, Accepted: 09 Jan 2012, Published: 30 Jun 2012

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.

3_2_179_185_800


Keywords


Dimerization; X-ray crystallography; Solvent-free conditions; Alkylidenemalononitrile; Acetophenone derivatives; Knoevenagel condensation

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DOI: 10.5155/eurjchem.3.2.179-185.562

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How to cite


Hameed, A.; Anwar, A.; Yousaf, S.; Khan, K.; Basha, F. Eur. J. Chem. 2012, 3(2), 179-185. doi:10.5155/eurjchem.3.2.179-185.562
Hameed, A.; Anwar, A.; Yousaf, S.; Khan, K.; Basha, F. 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(2), 179-185. doi:10.5155/eurjchem.3.2.179-185.562
Hameed, A., Anwar, A., Yousaf, S., Khan, K., & Basha, F. (2012). Tetra-n-butylammonium fluoride-mediated dimerization of (α-methylbenzylidene)malononitriles to form polyfunctional 5,6-dihydropyridines derivatives under solvent-free conditions. European Journal of Chemistry, 3(2), 179-185. doi:10.5155/eurjchem.3.2.179-185.562
Hameed, Abdul, Ayaz Anwar, Sammer Yousaf, Khalid Mohammed Khan, & Fatima Zahra Basha. "Tetra-n-butylammonium fluoride-mediated dimerization of (α-methylbenzylidene)malononitriles to form polyfunctional 5,6-dihydropyridines derivatives under solvent-free conditions." European Journal of Chemistry [Online], 3.2 (2012): 179-185. Web. 7 Dec. 2019
Hameed, Abdul, Anwar, Ayaz, Yousaf, Sammer, Khan, Khalid, AND Basha, Fatima. "Tetra-n-butylammonium fluoride-mediated dimerization of (α-methylbenzylidene)malononitriles to form polyfunctional 5,6-dihydropyridines derivatives under solvent-free conditions" European Journal of Chemistry [Online], Volume 3 Number 2 (30 June 2012)

DOI Link: https://doi.org/10.5155/eurjchem.3.2.179-185.562

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