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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 | Revised: 09 Jan 2012 | Accepted: 09 Jan 2012 | Published: 30 Jun 2012 | Issue Date: June 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.
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European Journal of Chemistry
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DOI: 10.5155/eurjchem.3.2.179-185.562
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Funding information
Higher Education Commission, Islamabad, Pakistan, HEJ, Research Institute of Chemistry, University of Karachi, Karachi
Citations
[1]. Ayaz Anwar, Abdul Hameed, Shahida Perveen, Maliha Uroos, Muhammad Iqbal Choudhary, Fatima Zahra Basha
1,1-Diphenyl-2-picrylhydrazyl radical scavenging activity of novel dihydropyridine derivatives
European Journal of Chemistry 5(1), 189, 2014
DOI: 10.5155/eurjchem.5.1.189-191.916
[2]. Abdul Hameed, Syeda Tazeen Zehra, Saba Abbas, Riffat Un Nisa, Tariq Mahmood, Khurshid Ayub, Mariya al-Rashida, Jürgen Bajorath, Khalid Mohammed Khan, Jamshed Iqbal
One-pot synthesis of tetrazole-1,2,5,6-tetrahydronicotinonitriles and cholinesterase inhibition: Probing the plausible reaction mechanism via computational studies
Bioorganic Chemistry 65, 38, 2016
DOI: 10.1016/j.bioorg.2016.01.004
[3]. Nafees Iqbal, Jamshed Hashim, Syed Abid Ali, Mariya al-Rashida Mariya al-Rashida, Rima D. Alharthy, Shakeel Ahmad, Khalid Mohammed Khan, Fatima Zahra Basha, Syed Tarique Moin, Abdul Hameed
Solvent-free 1H-tetrazole, 1,2,5,6-tetrahydronicotinonitrile and pyrazole synthesis using quinoline based ionic fluoride salts (QuFs): thermal and theoretical studies
RSC Advances 5(115), 95061, 2015
DOI: 10.1039/C5RA16075H
[4]. Oleg V. Ershov, Ivan N. Bardasov
Synthesis of pyridine derivatives containing a tricyanobutadiene motif (microreview)
Chemistry of Heterocyclic Compounds 53(11), 1178, 2017
DOI: 10.1007/s10593-018-2190-5
[5]. Abdul Hameed, Ayaz Anwar, Khalid Mohammed Khan, Rizwana Malik, Fernaz Shahab, Sadia Siddiq, Fatima Zahra Basha, Muhammad Iqbal Choudhary
Urease inhibition and anticancer activity of novel polyfunctional 5,6-dihydropyridine derivatives and their structure-activity relationship
European Journal of Chemistry 4(1), 49, 2013
DOI: 10.5155/eurjchem.4.1.49-52.701
[6]. Ayaz Anwar, Ruqaiyyah Siddiqui, Abdul Hameed, Muhammad R. Shah, Naveed A. Khan
Synthetic Dihydropyridines as Novel Antiacanthamoebic Agents
Medicinal Chemistry 16(7), 841, 2020
DOI: 10.2174/1573406415666190722113412
[7]. Zoltán Vincze, Péter Nemes
A novel strategy for the synthesis of 2,6-diaryl-1,2-dihydropyridines via 6π-electrocyclization
Tetrahedron 69(30), 6269, 2013
DOI: 10.1016/j.tet.2013.05.013
[8]. Hina Yousuf, Shahbaz Shamim, Khalid Mohammed Khan, Sridevi Chigurupati, Kanwal, Shehryar Hameed, Muhammad Naseem Khan, Muhammad Taha, Minhajul Arfeen
Dihydropyridines as potential α-amylase and α-glucosidase inhibitors: Synthesis, in vitro and in silico studies
Bioorganic Chemistry 96, 103581, 2020
DOI: 10.1016/j.bioorg.2020.103581
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DOI Link: https://doi.org/10.5155/eurjchem.3.2.179-185.562
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European Journal of Chemistry 2012, 3(2), 179-185 | doi: https://doi.org/10.5155/eurjchem.3.2.179-185.562 | Get rights and content
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