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

Main Article Content

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


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.


icon graph This Abstract was viewed 3634 times | icon graph Article PDF downloaded 1105 times

How to Cite
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.

Article Details

Crossref - Scopus - Google - European PMC

[1]. Knoevenagel, K. Ber. Dtsch. Chem. Ges. 1988, 31, 2596-2619.

[2]. Barnes, D. M.; Haight, A. R.; Hameury, T.; Mclaughlin, M. A.; Mei, J.; Tedrow, J. S.; Toma, J., D. R. Tetrahedron 2006, 62, 11311-11319.

[3]. Sharif, A.; Ahmad, E.; Munawar, M. A.; Jabeen, S.; Khan, M. U. A.; Begum, R.; Farrukh, A.; Ashraf, M.; Arshad, S.; Afza, N. J. Chem. Soc. Pak. 2011, 33, 578-786.

[4]. Bogdanowicz-Szwed, K.; Krasodomska, M. Monatsh. Chem. 2006, 137, 347-355.

[5]. Johnson, D. S.; Li, J. J. The Art of Drug Synthesis, John Wiley and Sons, Inc.: New Jersey, 2007.

[6]. Lichitsky, B. V.; Dudinov, A. A.; Krayushkin, M. M. Arkivoc 2001, 9, 73-79.

[7]. Dunkel, S.; Heb, U. J. Prakt. Chem. 1997, 339, 414-419.

[8]. Abdelrazek, F. M.; Metwally, M. H.; Kassab, N. A.; Sobhy, N. A.; Metz, P.; Jaeger, A. J. Heterocyclic Chem. 2010, 47, 348-388.

[9]. Corey, E. J.; Snider, B. B. J. Am. Chem. Soc. 1972, 94, 6190-6192

[10]. Cox, D. P.; Terpinski, J.; Lawrynowicz, W. J. Org. Chem. 1984, 49, 3216-3219.

[11]. Jacobi, P. A.; Brielmann, H. L.; Hauck, S. I. J. Org. Chem. 1996, 61, 5013-5023.

[12]. Yasuhara, A.; Kanamori, Y.; Kaneko, M.; Numata, A.; Kondo, Y.; Sakamoto, T. J. Chem. Soc., Perkin Trans. I 1999, 529-534.

[13]. Hiroya, K.; Jouka, R.; Kameda, M.; Yasuhara, A.; Sakamoto, T. Tetrahedron 2001, 57, 9697-9710.

[14]. Chung, K. -H.; Moon, B. -C.; Lim, C. H.; Kim, J. P.; Lee, J. H.; Chi, D. Y. Bull. Korean Chem. Soc. 2006, 27, 1203-1205.

[15]. Amantini, D.; Beleggia, R.; Fringuelli, F.; Pizzo, F.; Vaccaro, L. J. Org. Chem. 2004, 69, 2896-2898.

[16]. Alden-Danforth, E.; Scerba, M. T.; Lectka, T. Org. Lett. 2008, 10, 4951-4953.
PMid:18850717 PMCid:2652256

[17]. Albanese, D.; Landini, D.; Penso, M.; Petricci, S. Synlett. 1999, 199-200.

[18]. Albanese, D.; Donghi, A.; Landini, D.; Lupi, V.; Penso, M. Green Chem. 2003, 5, 367-369.

[19]. Lee, H. -G.; Won, J. -E.; Kim, M. -J.; Park, S. -E.; Jung, K. -J.; Kim, B. R.; Lee, S. -G.; Yoon, Y. -J. J. Org. Chem. 2009, 74, 5675-5678.

[20]. Sheldrick, G. M. SHELXTL/PC version 5. 1; Siemens Analytical X-ray Instruments Inc.: Madison, WI, 1997.

[21]. Johnson, C. K. ORTEPII. Report ORNL-5138; Oak Ridge National Laboratory: Oak Ridge, TN, 1976.

[22]. Nanjo, K.; Suzuki, K.; Sekiya, M. Chem. Pharm. Bull. 1977, 25, 2396-4000.

[23]. Ohnishi, Y.; Kagami, M.; Numakunai, T.; Ohno, A. Chem. Lett. 1976, 915-916.

[24]. Quincoses, J.; Peseke, K. Quim. Tecnol. Quim. 1978, 6, 95-102.

Most read articles by the same author(s)

Most read articles by the same author(s)


Dimensions - Altmetric - scite_ - PlumX

Downloads and views


Download data is not yet available.


Metrics Loading ...
License Terms

License Terms


Copyright © 2024 by Authors. This work is published and licensed by Atlanta Publishing House LLC, Atlanta, GA, USA. The full terms of this license are available at and incorporate the Creative Commons Attribution-Non Commercial (CC BY NC) (International, v4.0) License ( By accessing the work, you hereby accept the Terms. This is an open access article distributed under the terms and conditions of the CC BY NC License, which permits unrestricted non-commercial use, distribution, and reproduction in any medium, provided the original work is properly cited without any further permission from Atlanta Publishing House LLC (European Journal of Chemistry). No use, distribution, or reproduction is permitted which does not comply with these terms. Permissions for commercial use of this work beyond the scope of the License ( are administered by Atlanta Publishing House LLC (European Journal of Chemistry).