European Journal of Chemistry

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

Article Sidebar

PDF
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.

1_3_232_235_800


icon graph This Abstract was viewed 1777 times | icon graph Article PDF downloaded 1346 times

How to Cite
(1)
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.

Article Details

Share
Links for Article


Crossref - Scopus - Google - European PMC
Crossref
Scopus
Google Scholar
Europe PMC
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

Supporting Agencies

Department of Chemistry, School of Science, Azzahra University, Vanak, Tehran, Iran
Most read articles by the same author(s)
TrendMD

Dimensions - Altmetric - scite_ - PlumX

Downloads and views

Downloads

Download data is not yet available.

Metrics

Metrics Loading ...
License Terms

License Terms

by-nc

Copyright © 2024 by Authors. This work is published and licensed by Atlanta Publishing House LLC, Atlanta, GA, USA. The full terms of this license are available at https://www.eurjchem.com/index.php/eurjchem/terms and incorporate the Creative Commons Attribution-Non Commercial (CC BY NC) (International, v4.0) License (http://creativecommons.org/licenses/by-nc/4.0). By accessing the work, you hereby accept the Terms. This is an open access article distributed under the terms and conditions of the CC BY NC License, which permits unrestricted non-commercial use, distribution, and reproduction in any medium, provided the original work is properly cited without any further permission from Atlanta Publishing House LLC (European Journal of Chemistry). No use, distribution, or reproduction is permitted which does not comply with these terms. Permissions for commercial use of this work beyond the scope of the License (https://www.eurjchem.com/index.php/eurjchem/terms) are administered by Atlanta Publishing House LLC (European Journal of Chemistry).