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Synthesis of Quinoxaline Using Silica Supported Phosphomolybdic Acid as Reusable Heterogeneous Catalyst
Corresponding Author(s) : D. Tejeswararao
Asian Journal of Chemistry,
Vol. 28 No. 11 (2016): Vol 28 Issue 11
Abstract
Using phosphomolybdic acid on silica as recyclable catalyst we have developed methodology for the synthesis of quinoxalines by condensation of phenacyl bromides and o-phenylene diamines in ClCH2CH2Cl at 80 °C. The phosphomolybdic acid-silica catalyst can be reused for three successive runs with slight decrease in yield.
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- Y. Kurasawa, G. Sakata and K. Makino, Heterocycles, 27, 2481 (1988); doi:10.3987/REV-88-397.
- R. Sarges, H.R. Howard, R.G. Browne, L.A. Lebel, P.A. Seymour and B.K. Koe, J. Med. Chem., 33, 2240 (1990); doi:10.1021/jm00170a031.
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- K.R. Justin Thomas, M. Velusamy, J.T. Lin, C.-H. Chuen and Y.-T. Tao, Chem. Mater., 17, 1860 (2005); doi:10.1021/cm047705a.
- Z. Zhao, D.D. Wisnoski, S.E. Wolkenberg, W.H. Leister, Y. Wang and C.W. Lindsley, Tetrahedron Lett., 45, 4873 (2004); doi:10.1016/j.tetlet.2004.04.144.
- S. Antoniotti and E. Dunach, Tetrahedron Lett., 43, 3971 (2002); doi:10.1016/S0040-4039(02)00715-3.
- S.K. Singh, P. Gupta, S. Duggineni and B. Kundu, Synlett, 2147 (2003); doi:10.1055/s-2003-42065.
- B. Madhav, S. Narayana Murthy, V. Prakash Reddy, K. Rama Rao and Y.V.D. Nageswar, Tetrahedron Lett., 50, 6025 (2009); doi:10.1016/j.tetlet.2009.08.033.
- H.M. Meshram, G. Santosh Kumar, P. Ramesh and B. Chennakesava Reddy, Tetrahedron Lett., 51, 2580 (2010); doi:10.1016/j.tetlet.2010.01.107.
- T. Aoyama, T. Takido and M. Kodomari, Synlett, 13, 2307 (2004); doi:10.1055/s-2004-832812.
- M. Bandyopadhyay, S. Mukherjee, R.R. Rodriguez and B.K. Banik, Molecules, 15, 4207 (2010); doi:10.3390/molecules15064207.
- S.A. Kotharkar and D.B. Shinde, J. Iranian Chem. Soc., 3, 267 (2006); doi:10.1007/BF03247218.
References
Y. Kurasawa, G. Sakata and K. Makino, Heterocycles, 27, 2481 (1988); doi:10.3987/REV-88-397.
R. Sarges, H.R. Howard, R.G. Browne, L.A. Lebel, P.A. Seymour and B.K. Koe, J. Med. Chem., 33, 2240 (1990); doi:10.1021/jm00170a031.
B. Solano, V. Junnotula, A. Marín, R. Villar, A. Burguete, E. Vicente, S. Pérez-Silanes, I. Aldana, A. Monge, S. Dutta, U. Sarkar and K.S. Gates, J. Med. Chem., 50, 5485 (2007); doi:10.1021/jm0703993.
J.D. Brown in eds.: C.E. Taylor and P. Wipf, The Chemistry of Heterocyclic Compounds Quinoxalines: Supplements II; John Wiley & Sons, New Jersey (2004).
A. Katoh, T. Yoshida and J. Ohkanda, Heterocycles, 52, 911 (2000); doi:10.3987/COM-99-S61.
S. Dailey, W.J. Feast, R.J. Peace, I.C. Sage, S. Till and E.L. Wood, J. Mater. Chem., 11, 2238 (2001); doi:10.1039/b104674h.
M.J. Crossley and L.A. Johnston, Chem. Commun., 13, 1122 (2002); doi:10.1039/b111655j.
K.R. Justin Thomas, M. Velusamy, J.T. Lin, C.-H. Chuen and Y.-T. Tao, Chem. Mater., 17, 1860 (2005); doi:10.1021/cm047705a.
Z. Zhao, D.D. Wisnoski, S.E. Wolkenberg, W.H. Leister, Y. Wang and C.W. Lindsley, Tetrahedron Lett., 45, 4873 (2004); doi:10.1016/j.tetlet.2004.04.144.
S. Antoniotti and E. Dunach, Tetrahedron Lett., 43, 3971 (2002); doi:10.1016/S0040-4039(02)00715-3.
S.K. Singh, P. Gupta, S. Duggineni and B. Kundu, Synlett, 2147 (2003); doi:10.1055/s-2003-42065.
B. Madhav, S. Narayana Murthy, V. Prakash Reddy, K. Rama Rao and Y.V.D. Nageswar, Tetrahedron Lett., 50, 6025 (2009); doi:10.1016/j.tetlet.2009.08.033.
H.M. Meshram, G. Santosh Kumar, P. Ramesh and B. Chennakesava Reddy, Tetrahedron Lett., 51, 2580 (2010); doi:10.1016/j.tetlet.2010.01.107.
T. Aoyama, T. Takido and M. Kodomari, Synlett, 13, 2307 (2004); doi:10.1055/s-2004-832812.
M. Bandyopadhyay, S. Mukherjee, R.R. Rodriguez and B.K. Banik, Molecules, 15, 4207 (2010); doi:10.3390/molecules15064207.
S.A. Kotharkar and D.B. Shinde, J. Iranian Chem. Soc., 3, 267 (2006); doi:10.1007/BF03247218.