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Copyright (c) 2014 Syed Salman Shafqat1, Misbahul Ain Khan2, Azham Zulkharnain4, Sinin Hamdan1, Andrew Ragai Henry Rigit1, Amir Azam Khan1
This work is licensed under a Creative Commons Attribution 4.0 International License.
Synthesis of Arylidene Propanedioic Acids by Knoevenagel Condensation for use in Ceramic Sols
Corresponding Author(s) : Syed Salman Shafqat1
Asian Journal of Chemistry,
Vol. 26 No. 24 (2014)
Abstract
This paper is primarily concerned with the synthesis of arylidene propanedioic acids by Knoevenagel condensation. Generally organic bases pyridine and piperidine are used as catalyst in Knoevenagel condensation which are costly and health hazard. In this research work, Knoevenagel condensation of various aromatic aldehydes (benzaldehyde, salicylaldehyde and p-chlorobenzaldehyde) and active methylenes (malonic acid and ethyl acetoacetate) was carried out in the presence of amino acids (glycine, lysine, hippuric acid, methionine and leucine) as catalyst. Using salicylaldehyde gave coumarin-3-carboxylic acid, a solvent free synthesis. These products were isolated and purified and were characterized through melting points, TLC, IR, mass and 1H NMR. These acids are synthesized for eventual development of organically modified ceramic nano powders.
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References
G. Jones, Organic Reactions Wiley, New York (1967).
F. Chaudhry, N. Asif, M.N. Khan, J. Ribeiro, A.Q. Ather, S. Hina, M.A. Munawar, M. Nasrullah, Q.T. Ain, F. Suhail and M.A. Khan, Asian J. Chem., 25, 7879 (2013).
F. Ijaz, M.N. Khan, S. Naureen, M.A. Khan, M.A. Munawar and A.M.R. Bernardino, Asian J. Chem., 24, 5114 (2012).
A.M. Zafar, M.N. Khan, M. Azad, M.A. Munawar and M.A. Khan, Asian J. Chem., 25, 3244 (2013).
T. Ohara, T. Sato, N. Shimizu, G. Prescher, H. Schwind, O. Weiberg, K. Marten and H. Greim, Ullmann's Encyclopedia of Industrial Chemistry (2003).
K. Budde, F. Quella, A. Mathes, W. Melchior, H. Müller, O. Nuyken and S. Spiegel, Die Angew. Makromol. Chem., 194, 103 (1992).
C.-L. Lin and W.-Y. Chiu, J. Polym. Sci. A Polym. Chem., 44, 1648 (2006).
A. Bhattacharya, A. De and S.N. Bhattacharyya, Synth. Met., 65, 35 (1994).
W. Wang, L. Lu, T. Chen and M. Rao, J. Appl. Polym. Sci., 126, 974 (2012).
Q. Li, J. Wu, Z. Tang, Y. Xiao, M. Huang and J. Lin, Electrochim. Acta, 55, 2777 (2010).
C.S. Marvel, L.E. Coleman and G.P. Scott, J. Org. Chem., 20, 1785 (1955).
F.S. Prout, J. Org. Chem., 18, 928 (1953).
K. Sakthivel, W. Notz, T. Bui and C.F. Barbas, J. Am. Chem. Soc., 123, 5260 (2001).
L.A. Al-Momani, ARKIVOC, 101 (2012).
B. List, Tetrahedron, 58, 5573 (2002).
A.J. Cobb, D.M. Shaw, D.A. Longbottom, J.B. Gold and S.V. Ley, Org. Biomol. Chem., 3, 84 (2005).
N.V. Shitole, K.F. Shelke, S.S. Sonar, S.A. Sadaphal, B.B. Shingate and M.S. Shingare, Chem. Inform., 41, i (2010).
S. Patel, A. Bandyopadhyay, V. Vijayabaskar and A.K. Bhowmick, J. Mater. Sci., 41, 927 (2006).
J.T. Park, J.A. Seo, S.H. Ahn, J.H. Kim and S.W. Kang, J. Ind. Eng. Chem., 16, 517 (2010).
C.A. Kingsbury, D. Draney, A. Sopchik, W. Rissler and D. Durham, J. Org. Chem., 41, 3863 (1976).
J.S. Bindra, Enkephalinase Enzyme Inhibiting Compounds, US Patent 4,329,495 (1982).
L.L. Woods and J. Sapp, J. Org. Chem., 30, 312 (1965).