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Synthesis of Novel 2,4-Di(o-Hydroxyphenyl)-6-substituted Amino-1,3,5-triazine
Corresponding Author(s) : Junrong Jiang
Asian Journal of Chemistry,
Vol. 27 No. 5 (2015): Vol 27 Issue 5
Abstract
Seven novel 1,3,5-triazine derivatives were synthesized in good to high yields (69.19-91.15 %) by the reaction of substituted guanidine with 2-(2-hydroxyphenyl)-4H-benzo[e][1,3]oxazin-4-one in ethanol. The products were recrystallized from ethanol or ethanol-DMF mixture and their structures were confirmed by 1H NMR and FT-IR.
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- G.H. Kuo, A. Deangelis, S. Emanuel, A. Wang, Y. Zhang, P.J. Connolly, X. Chen, R.H. Gruninger, C. Rugg, A.F. Pesquera, S.A. Middleton, L. Jolliffe and W.V. Murray, J. Med. Chem., 48, 4535 (2005); doi:10.1021/jm040214h.
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- E. Piera, F. Comelles, P. Erra and M.R. Infante, J. Chem. Soc., Perkin Trans. II, 335 (1998); doi:10.1039/A705565J.
- D. Schaubroeck, J. De Baets, T. Desmet, P. Dubruel, E. Schacht, L. Van Vaeck and A. Van Calster, Appl. Surf. Sci., 256, 6269 (2010); doi:10.1016/j.apsusc.2010.04.003.
- X.C. Wang, G. Wang and X.C. Jiao, Agrochemical, 50, 320 (2011).
- Y.F. Sun, D.F. Zhao and H.S. Freeman, Dyes Pigments, 74, 608 (2007); doi:10.1016/j.dyepig.2006.04.001.
- Y.G. Huang, Y.Q. Zhang and J.M. Shreeve, Chem. Eur. J., 17, 1538 (2011); doi:10.1002/chem.201002363.
- J.A. Mikroyannidis, S.S. Sharma, Y.K. Vijay and G.D. Sharma, ACS Appl. Mater. Interfaces, 2, 270 (2010); doi:10.1021/am9006897.
- A. García, B. Insuasty, M.Á. Herranz, R. Martínez-Álvarez and N. Martín, Org. Lett., 11, 5398 (2009); doi:10.1021/ol902203t.
- A.R. Silva, V. Budarin, J.H. Clark, C. Freire and B. de Castro, Carbon, 45, 1951 (2007); doi:10.1016/j.carbon.2007.06.013.
- G. Blotny, Tetrahedron, 62, 9507 (2006); doi:10.1016/j.tet.2006.07.039.
- T. Bolle, A. Valet, D.G. Leppard, S.M. Andrews, R. Ravichandran, M. Grob and D. Simon, US Patent 2005075465 (2005).
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- K.D.Burdeska, EP 0497734(1992).
- D. Reinehr and J.P. Bacher, US Patent 5478935(1995).
- R.B. Gupta, D.J. Jakiela, S. Venimadhavan, R.C. Cappadona and V.K. Pai, US Patent 2004204585 (2004).
- R.B. Gupta, D.J. Jakiela, S. Venimadhvan, R.C. Cappadona and V.K. Pai, US Patent 6486317(2002).
- C.A. Migdal, J.B. Hines and E.W. Kluger, US Patent 4826978(1989).
- H. Henneberger and M. Wagner, US Patent 543813(1995).
- M. Sun, H.T. Wei, C.L. Shi, Y.G. Zheng and M. Ji, Chin. J. New Drugs, 18, 850 (2009).
References
G.H. Kuo, A. Deangelis, S. Emanuel, A. Wang, Y. Zhang, P.J. Connolly, X. Chen, R.H. Gruninger, C. Rugg, A.F. Pesquera, S.A. Middleton, L. Jolliffe and W.V. Murray, J. Med. Chem., 48, 4535 (2005); doi:10.1021/jm040214h.
Y.F. Zhou, Z.X. Sun, J.M. Froelich, T. Hermann and D. Wall, Bioorg. Med. Chem. Lett., 16, 5451 (2006); doi:10.1016/j.bmcl.2006.07.052.
E. Piera, F. Comelles, P. Erra and M.R. Infante, J. Chem. Soc., Perkin Trans. II, 335 (1998); doi:10.1039/A705565J.
D. Schaubroeck, J. De Baets, T. Desmet, P. Dubruel, E. Schacht, L. Van Vaeck and A. Van Calster, Appl. Surf. Sci., 256, 6269 (2010); doi:10.1016/j.apsusc.2010.04.003.
X.C. Wang, G. Wang and X.C. Jiao, Agrochemical, 50, 320 (2011).
Y.F. Sun, D.F. Zhao and H.S. Freeman, Dyes Pigments, 74, 608 (2007); doi:10.1016/j.dyepig.2006.04.001.
Y.G. Huang, Y.Q. Zhang and J.M. Shreeve, Chem. Eur. J., 17, 1538 (2011); doi:10.1002/chem.201002363.
J.A. Mikroyannidis, S.S. Sharma, Y.K. Vijay and G.D. Sharma, ACS Appl. Mater. Interfaces, 2, 270 (2010); doi:10.1021/am9006897.
A. García, B. Insuasty, M.Á. Herranz, R. Martínez-Álvarez and N. Martín, Org. Lett., 11, 5398 (2009); doi:10.1021/ol902203t.
A.R. Silva, V. Budarin, J.H. Clark, C. Freire and B. de Castro, Carbon, 45, 1951 (2007); doi:10.1016/j.carbon.2007.06.013.
G. Blotny, Tetrahedron, 62, 9507 (2006); doi:10.1016/j.tet.2006.07.039.
T. Bolle, A. Valet, D.G. Leppard, S.M. Andrews, R. Ravichandran, M. Grob and D. Simon, US Patent 2005075465 (2005).
J. Haase, T. Ehlis, E. Borsos, D. Huglin and B. Herzog, US Patent 2005129632 (2005).
D. Reinehr, G. Metzger, P. Michaelis and H. Luther, US Patent 2007274933 (2007).
K.D.Burdeska, EP 0497734(1992).
D. Reinehr and J.P. Bacher, US Patent 5478935(1995).
R.B. Gupta, D.J. Jakiela, S. Venimadhavan, R.C. Cappadona and V.K. Pai, US Patent 2004204585 (2004).
R.B. Gupta, D.J. Jakiela, S. Venimadhvan, R.C. Cappadona and V.K. Pai, US Patent 6486317(2002).
C.A. Migdal, J.B. Hines and E.W. Kluger, US Patent 4826978(1989).
H. Henneberger and M. Wagner, US Patent 543813(1995).
M. Sun, H.T. Wei, C.L. Shi, Y.G. Zheng and M. Ji, Chin. J. New Drugs, 18, 850 (2009).