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A Simple and Straightforward Synthesis of Cinnamic acids and Ylidene Malononitriles via Knoevenagel Condensation Employing DABCO as Catalyst
Corresponding Author(s) : K. Nagalakshmi
Asian Journal of Chemistry,
Vol. 29 No. 7 (2017): Vol 29 Issue 7
Abstract
An efficient method for the synthesis of substituted cinnamic acid and ylidene malanonitriles is developed via Knoevenagel condensation of aromatic aldehydes with malonic acid and malononitrile in the presence of catalytic amounts of DABCO. This method has many advantages, such as mild reaction conditions, excellent yields, short reaction times and no furthur purification required.
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- J. Song and M. Hesse, Tetrahedron, 49, 6797 (1993); https://doi.org/10.1016/S0040-4020(01)80423-3.
- U. Marquardt, D. Schmid and G. Jung, Synlett, 8, 1131 (2000); https://doi.org/10.1055/s-002-411.
- R.K. Callow and N.C. Johnston, Bee World, 41, 152 (1960); https://doi.org/10.1080/0005772X.1960.11096785.
- T. Sasaki, K. Minamoto, T. Suzuki and S. Yamashita, Tetrahedron, 36, 865 (1980); https://doi.org/10.1016/0040-4020(80)80036-6.
- Y. Peng and G. Song, Green Chem., 5, 704 (2003); https://doi.org/10.1039/B310388A.
- E. knovenagel, Ber., 31, 2596 and 2619 (1898). https://doi.org/10.1002/cber.18980310308.
- J. Mc Nulty, J.A. Steere and S. Wolf, Tetrahedron Lett., 39, 8013 (1998); https://doi.org/10.1016/S0040-4039(98)01789-4.
- P.S. Kwon, Y.M. Kim, C.J. Kang, T.W. Kwon, S.-K. Chung and Y.-T. Chang, Synth. Commun., 27, 4091 (1997); https://doi.org/10.1080/00397919708005456.
- Y. Peng and G. Song, Green Chem., 5, 704 (2003); https://doi.org/10.1039/B310388A.
- S.-K. Tian, R. Hong and L. Deng, J. Am. Chem. Soc., 125, 9900 (2003); https://doi.org/10.1021/ja036222p.
- D. Basavaiah, A.J. Rao and T. Satyanarayana, Chem. Rev., 103, 811 (2003); https://doi.org/10.1021/cr010043d.
- S.K. Tian, R. Hong and L. Deng, J. Am. Chem. Soc., 125, 9900 (2003); https://doi.org/10.1021/ja036222p.
- J.A. Linn, E.W. McLean and J.L. Kelley, J. Chem. Soc. Chem. Commun., 913 (1994); https://doi.org/10.1039/C39940000913
References
J. Song and M. Hesse, Tetrahedron, 49, 6797 (1993); https://doi.org/10.1016/S0040-4020(01)80423-3.
U. Marquardt, D. Schmid and G. Jung, Synlett, 8, 1131 (2000); https://doi.org/10.1055/s-002-411.
R.K. Callow and N.C. Johnston, Bee World, 41, 152 (1960); https://doi.org/10.1080/0005772X.1960.11096785.
T. Sasaki, K. Minamoto, T. Suzuki and S. Yamashita, Tetrahedron, 36, 865 (1980); https://doi.org/10.1016/0040-4020(80)80036-6.
Y. Peng and G. Song, Green Chem., 5, 704 (2003); https://doi.org/10.1039/B310388A.
E. knovenagel, Ber., 31, 2596 and 2619 (1898). https://doi.org/10.1002/cber.18980310308.
J. Mc Nulty, J.A. Steere and S. Wolf, Tetrahedron Lett., 39, 8013 (1998); https://doi.org/10.1016/S0040-4039(98)01789-4.
P.S. Kwon, Y.M. Kim, C.J. Kang, T.W. Kwon, S.-K. Chung and Y.-T. Chang, Synth. Commun., 27, 4091 (1997); https://doi.org/10.1080/00397919708005456.
Y. Peng and G. Song, Green Chem., 5, 704 (2003); https://doi.org/10.1039/B310388A.
S.-K. Tian, R. Hong and L. Deng, J. Am. Chem. Soc., 125, 9900 (2003); https://doi.org/10.1021/ja036222p.
D. Basavaiah, A.J. Rao and T. Satyanarayana, Chem. Rev., 103, 811 (2003); https://doi.org/10.1021/cr010043d.
S.K. Tian, R. Hong and L. Deng, J. Am. Chem. Soc., 125, 9900 (2003); https://doi.org/10.1021/ja036222p.
J.A. Linn, E.W. McLean and J.L. Kelley, J. Chem. Soc. Chem. Commun., 913 (1994); https://doi.org/10.1039/C39940000913