European Journal of Chemistry

DABCO as an efficient catalyst for the synthesis of 3-cyano-2(1H)-pyridinones and their 2-imino analogues

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Published: Sep 29, 2010
DOI: https://doi.org/10.5155/eurjchem.1.3.232-235.112
Keywords:
1, 4-Diaza-bicyclo[2, 2, 2]octane, Cyano-2(1H)-pyridinones, Cyano-2(1H)-iminopyridines, 3, 4-Dimethoxyacetophenone, DABCO, Catalyst
Section
Short Communication
Issue
Vol. 1 No. 3 (2010): September 2010
Dates
Received 2010-05-17
Accepted 2010-07-08
Published 2010-09-29


Main Article Content

Yahia Shirazi Beheshtia
Department of Chemistry, School of Science, Azzahra University, Vanak, Tehran, IR19569, Iran
Maliheh Khorshidi
Department of Chemistry, School of Science, Azzahra University, Vanak, Tehran, IR19569, Iran
Majid Momahed Heravi
Department of Chemistry, School of Science, Azzahra University, Vanak, Tehran, IR19569, Iran
Bita Baghernejad
Department of Chemistry, School of Science, Azzahra University, Vanak, Tehran, IR19569, Iran

Abstract

3-cyano-2(1H)-pyridinones and their 2-imino analogues have been synthesized in good yields via a one-pot multi-component reaction of 3,4-dimethoxyacetophenone, malononitrile or ethylcyanoacetate, ammonium acetate and various aldehydes in the presence of  1,4-diaza-bicyclo[2,2,2]octane (DABCO) in ethanol. DABCO has been widely used as a catalyst for the organic reactions and we selected it as an efficient catalyst to synthesis of 3-cyano-pyridines. All products were characterized by melting point, IR, 1H NMR and GC/MS studies.

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Beheshtia, Y. S.; Khorshidi, M.; Heravi, M. M.; Baghernejad, B. DABCO As an Efficient Catalyst for the Synthesis of 3-Cyano-2(1H)-Pyridinones and Their 2-Imino Analogues. Eur. J. Chem. 2010, 1, 232-235.

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References

[1]. Roth, H. J.; Kleemann, A. Pharmaceutical Chemistry; Eds.; Vol. 1: Drug Synthesis; John Wiley & Sons: New York, 1988.

[2]. Doe, K.; Avasthi, K.; Pratap, R.; Bakuni, D. S.; Joshi, M. N. Indian. J. Chem. 1990, 29, 459-463.

[3]. Shishoo, C. J.; Devani, M. B.; Bhadti, V. S.; Ananthan, S.; Ullas, G. V. Tetrahedron Lett. 1983, 24, 4611-4612.
doi:10.1016/S0040-4039(00)85969-9

[4]. Barili, P. L.; Biagi, G.; Livi, O.; Mucci, L.; Scartoni, V. J. Heterocycl. Chem. 1987, 24, 997-1001.
doi:10.1002/jhet.5570240419

[5]. Attia, A.; Michael, M. Pharmazie. 1982, 37, 551-553.
PMid:6755494

[6]. Kambe, S.; Saito, K. Synthesis. 1980, 5, 365-368.

[7]. Domling, A.; Ugi, I. Angew. Chem. Int. Ed. 2000, 39, 3168-3210.
doi:10.1002/1521-3773(20000915)39:18<3168::AID-ANIE3168>3.0.CO;2-U

[8]. Domling, A. Comb. Chem. 1998, 1, 1-22.

[9]. Pan. J. F.; Chen, K. Tetrahedron Lett. 2004, 45, 2541-2543.
doi:10.1016/j.tetlet.2004.02.001

[10]. Sheen, W. C.; Lazanov, M.; Rejic, O. Tetrahedron Lett. 2003, 44, 6943-6945.
doi:10.1016/S0040-4039(03)01711-8

[11]. Takkewaki, T.; Beck, L. W.; Danis, M. E. Micropor. Mesopor. Mater. 1999, 33, 197-207.
doi:10.1016/S1387-1811(99)00138-9

[12]. Veeraraghavan, P.; Michael, R.; Rudd, T.; Reddy, M. V. R. Tetrahedron Lett. 1999, 40, 3819-3822.
doi:10.1016/S0040-4039(99)00630-9

[13]. Basavaiah, D.; Bharathi, T. K.; Gawzeswaie, V. V. L. Tetrahedron Lett. 1987, 28, 4352-4651.

[14]. Basavaiah, D.; Gawriswari; V. V. L.; Baharathine, T. K. Tetrahedron Lett. 1987, 28, 4591-4592.
doi:10.1016/S0040-4039(00)96573-0

[15]. Bamoharram, F. F.; Heravi, M. M.; Roshani, M.; Gharib, A.; Jahangir, M. Appl. Catal. 2006, 302, 42-47.
doi:10.1016/j.apcata.2005.12.021

[16]. Heravi, M. M.; Hekmatshoar, R.; Pedram, L. J. Mol. Catal. A. Chem. 2005, 231, 89-91.
doi:10.1016/j.molcata.2005.01.005

[17]. Heravi, M. M.; Bakhtiari, K.; Oskooie, H. A. J. Chin. Chem. Soc. 2007, 54, 579-581.

[18]. Heravi, M. M.; Oskooie, H. A.; Baghernejad, B. J. Chin. Chem. Soc. 2007, 54, 767-770.

[19]. Lin, X.; Poeppelmeier, K. R.; Weitz, E. Appl. Catal. A: Gen. 2010, 381, 114-120.
doi:10.1016/j.apcata.2010.03.049

[20]. Abadi, A.; Al-Deeb, O.; Al-Afify, A.; El-Kashef, H. Farmaco II 1999, 54, 195-201.

[21]. Heravi, M. M.; Beheshtia, Y. S.; Khorshidi, M.; Baghernejad, B.; Bamoharram, F. Chin. J. Chem. 2009, 27, 569-572.
doi:10.1002/cjoc.200990093

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Department of Chemistry, School of Science, Azzahra University, Vanak, Tehran, Iran
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