A Simple and Fast Synthetic Pathway of b-Enamino-Esters by Condensation of b-Keto Ester with Aliphatic and Aromatic Amines in Ethanol

Y. Kouadri; M.R. Ouahrani; B.E. Missaoui; F. Chebrouk; N. Gherraf

doi:10.14233/ajchem.2015.18324

Issue

Vol. 27 No. 7 (2015): Vol 27 Issue 7, 2015

Issue Published : March 29, 2015

This work is licensed under a Creative Commons Attribution 4.0 International License.

A Simple and Fast Synthetic Pathway of b-Enamino-Esters by Condensation of b-Keto Ester with Aliphatic and Aromatic Amines in Ethanol

https://doi.org/10.14233/ajchem.2015.18324

Y. Kouadri

Laboratoire de Chimie Organique, Université KASDI Merbah, Ouargla, Algéria; Laboratoire VPRS Université KASDI Merbah, Ouargla, Algéria

M.R. Ouahrani

Laboratoire de Chimie Organique, Université KASDI Merbah, Ouargla, Algéria; Laboratoire VPRS Université KASDI Merbah, Ouargla, Algéria

B.E. Missaoui

Laboratoire de Chimie Organique, Université KASDI Merbah, Ouargla, Algéria; Laboratoire VPRS Université KASDI Merbah, Ouargla, Algéria

F. Chebrouk

Centre de Recherche Scientifique et Technique en Analyses Physico-Chimiques (CRAPC), BP 248, Alger 16004, Algéria

N. Gherraf

Laboratoire des Ressources Naturelles et Aménagement des Milieux Sensibles, Université Larbi ben M'hidi, Oum Elbouaghi, Algeria

Corresponding Author(s) : Y. Kouadri

hadadberini@yahoo.com; ngherraf@yahoo.com

Asian Journal of Chemistry, Vol. 27 No. 7 (2015): Vol 27 Issue 7, 2015
Article Published : March 30, 2015

Abstract

The b-keto ester undergoes condensation reactions with aliphatic and aromatic amines in ethanol to give high-yielding b-enamino ester. The method is simple, cost-effective and environmentally benign. Structural characterization of the synthesized compounds was carried out by spectroscopic methods (¹H NMR, ¹³C NMR and DEPT).

Keywords

b-Keto esters β-Enamin oesters

Kouadri, Y., Ouahrani, M., Missaoui, B., Chebrouk, F., & Gherraf, N. (2015). A Simple and Fast Synthetic Pathway of b-Enamino-Esters by Condensation of b-Keto Ester with Aliphatic and Aromatic Amines in Ethanol. Asian Journal of Chemistry, 27(7), 2575–2578. https://doi.org/10.14233/ajchem.2015.18324

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J.P. Michael, C.B. de Koning, G.D. Hosken and T.V. Stanbury, Tetrahedron, 57, 9635 (2001); doi:10.1016/S0040-4020(01)00964-4.

A.C. Spivey, R. Srikaran, C.M. Diaper and D.J. Turner, Org. Biomol. Chem., 1, 1638 (2003); doi:10.1039/b303064d.

M.C. Bagley, J.W. Dale, X. Xiong and J. Bower, Org. Lett., 5, 4421 (2003); doi:10.1021/ol0357144.

J. Moreau, A. Duboc, C. Hubert, J.-P. Hurvois and J.-L. Renaud, Tetrahedron Lett., 48, 8647 (2007); doi:10.1016/j.tetlet.2007.10.040.

A.Z.A. Elassar and A.A. El-Khair, Tetrahedron, 59, 8463 (2003); doi:10.1016/S0040-4020(03)01201-8.

J.P. Michael, C.B. de Koning, G.D. Hosken and T.V. Stanbury, Tetrahedron, 57, 9635 (2001); doi:10.1016/S0040-4020(01)00964-4.

C. Cimarelli, G. Palmieri and E. Volpini, Synth. Commun., 31, 2943 (2001); doi:10.1081/SCC-100105666.

J.L. Aceña, O. Arjona, R. Mañas and J. Plumet, J. Org. Chem., 65, 2580 (2000); doi:10.1021/jo991468r.

G. Li, K. Watson, R.W. Buckheit and Y. Zhang, Org. Lett., 9, 2043 (2007); doi:10.1021/ol070748n.

A. Arcadi, G. Bianchi, S.D. Giuseppe and F. Marinelli, Green Chem., 5, 64 (2003); doi:10.1039/b210165c.

A.R. Khosropour, M.M. Khodaei and M.A. Kookhazadeh, Tetrahedron Lett., 45, 1725 (2004); doi:10.1016/j.tetlet.2003.12.093.

G. Bartoli, M. Bosco, M. Locatelli, E. Marcantoni, P. Melchiorre and L. Sambri, Synlett, 239 (2004); doi:10.1055/s-2003-44974.

M.M. Khodaei, A.R. Khosropour and M. Kookhazadeh, Synlett, 1980 (2004); doi:10.1055/s-2004-830879.

B. Das, K. Venkateswarlu, A. Majhi, M.R. Reddy, K.N. Reddy, Y.K. Rao, K. Ravikumar and B. Sridhar, J. Mol. Catal. Chem., 246, 276 (2006); doi:10.1016/j.molcata.2005.11.045.

A.H. Mohamed, B. Brahim, L. El Firdoussi and M.A. Ali, Am. J. Chem., 2, 271 (2012); doi:10.5923/j.chemistry.20120205.05.

R. Thorwirth and A. Stolle, Synlett, 2200 (2011); doi:10.1055/s-0030-1261179.

N. Panda and R. Mothkuri, J. Org. Chem., 77, 9407 (2012); doi:10.1021/jo301772f.

S. Kramer, K. Dooleweerdt, A.T. Lindhardt, M. Rottländer and T. Skrydstrup, Org. Lett., 11, 4208 (2009); doi:10.1021/ol901565p.

X. Zhang, B. Yang, G. Li, X. Shu, D.C. Mungra and J. Zhu, Synlett, 23, 622 (2012); doi:10.1055/s-0031-1290341.

Y.S. Chun, Y.O. Ko, H. Shin and S. Lee, Org. Lett., 11, 3414 (2009); doi:10.1021/ol901241s.

J.H. Lee, B.S. Choi, J.H. Chang, H.B. Lee, J.-Y. Yoon, J. Lee and H. Shin, J. Org. Chem., 72, 10261 (2007); doi:10.1021/jo701743m.

Issue

Vol. 27 No. 7 (2015): Vol 27 Issue 7, 2015

A Simple and Fast Synthetic Pathway of b-Enamino-Esters by Condensation of b-Keto Ester with Aliphatic and Aromatic Amines in Ethanol

Corresponding Author(s) : Y. Kouadri

Abstract

Keywords

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