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Synthesis of 1,9-Diazaphenoxazine Carboxamide Derivatives via Buchwald-Hartwig Amidation Protocol
Corresponding Author(s) : D.I. Ugwu
Asian Journal of Chemistry,
Vol. 27 No. 9 (2015): Vol 27 Issue 9
Abstract
Tandem amidation catalyzed synthesis of linear diazaphenoxazine carboxamide derivatives (18a-e) is reported. This was achieved by the reaction of 2-amino-3-hydroxypyridine (11) and 2,3,5-trichloropyridine (12) in aqueous basic medium to afford 3-chloro-1,9-diazaphenoxazine (13) as white solid crystals. Compound 13 was then subjected to Buchwald-Hartwig amidation coupling reaction with various carboxamides (17a-e) in the presence of 1,4-bis(2-hydroxyl-3,5-di-tert-butyl benzyl)piperazine (16) as ligand, Pd(OAc)2 as palladium source catalyst, K2CO3 as base and 50:50 DMF and toluene as solvent at 110 ºC for 2 h to afford the linear diazaphenoxazine carboxamide derivatives (18a-e) in good to excellent yield. The water mediated pre-activation of the catalyst was monitored visually using colour change from yellow to black. The compounds were characterized using UV-visible, FTIR, 1H NMR, 13C NMR spectroscopy and elemental analysis.
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- J.K. Horton, K.N. Thimmaiah, F.C. Harwood, S.J.F. Kutte and P.J. Houghton, Pharmocol. Abstr., 44, 552 (1993).
- C.O. Okafor, Heterocycles, 7, 391 (1977); doi:10.3987/S-1977-01-0391.
- K. Fries and P. Ochwat, Chem. Abstr., 1291(56B), 3334 (1923).
- C.O. Okafor, Tetrahedron, 42, 2771 (1986); doi:10.1016/S0040-4020(01)90564-2.
- H. Prinz, B. Chamasmani, K. Vogel, K.J. Bohm, B. Aicher, M. Gerlach, E.G. Gunther, P. Amon, I. Ivanov and K. Muller, J. Med. Chem., 54, 4247 (2011); doi:10.1021/jm200436t.
- A. Nowakowska-Oleksy, J. Soloducho and J. Cabaj, J. Fluoresc., 21, 169 (2011); doi:10.1007/s10895-010-0701-6.
- B.C. Raju, K.V. Prasad, G. Saidachary and B. Sridhar, Org. Lett., 16, 420 (2014); doi:10.1021/ol4033122.
- I. Thome and C. Bolm, Org. Lett., 14, 1892 (2012); doi:10.1021/ol3005134.
- M.C. Reddy, An Improved Process for the Preparation of Antidiabetic Phenoxazine Compounds, WO 2003008397A1 2003 (2003).
- J. Jose and K. Burgess, Tetrahedron, 62, 11021 (2006); doi:10.1016/j.tet.2006.08.056.
- K. Hayashi, T. Hayashi, K. Miyazawa and A. Tomoda, J. Pharm. Sci., 114, 85 (2010); doi:10.1254/jphs.10027FP.
- T. Shimamoto, A. Tomoda, R. Ishida and K. Ohyashiki, Clin. Cancer Res., 7, 704 (2001).
- A. Iwata, T. Yamaguchi, K. Sato, N. Yoshitake and A. Tomoda, Biol. Pharm. Bull., 28, 905 (2005); doi:10.1248/bpb.28.905.
- M. Idries and A.-M. Abeed, Qua Medicinal J., 4, 120 (2010).
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- K. Persson, M. Sc. Thesis, Department of Chemistry, Colorado State University (2012).
- K. Kohli, S.K. Srivastava and S.D. Srivastava, J. Applicable Chem., 3, 525 (2014).
- J.P. Wolfe and S.L. Buchwald, Org. Khim. Synth. Cok., 10, 423 (2004).
- X. Huang, K.W. Anderson, D. Zim, L. Jiang, A. Klapars and S.L. Buchwald, J. Am. Chem. Soc., 125, 6653 (2003); doi:10.1021/ja035483w.
- S. Mohanty, D. Suresh, M.S. Balakrishna and J.T. Mague, Tetrahedron, 64, 240 (2008); doi:10.1016/j.tet.2007.10.081.
- K.W. Anderson, R.E. Tundel, T. Ikawa, R.A. Altman and S.L. Buchwald, Angew. Chem. Int. Ed., 45, 6523 (2006); doi:10.1002/anie.200601612.
References
J.K. Horton, K.N. Thimmaiah, F.C. Harwood, S.J.F. Kutte and P.J. Houghton, Pharmocol. Abstr., 44, 552 (1993).
C.O. Okafor, Heterocycles, 7, 391 (1977); doi:10.3987/S-1977-01-0391.
K. Fries and P. Ochwat, Chem. Abstr., 1291(56B), 3334 (1923).
C.O. Okafor, Tetrahedron, 42, 2771 (1986); doi:10.1016/S0040-4020(01)90564-2.
H. Prinz, B. Chamasmani, K. Vogel, K.J. Bohm, B. Aicher, M. Gerlach, E.G. Gunther, P. Amon, I. Ivanov and K. Muller, J. Med. Chem., 54, 4247 (2011); doi:10.1021/jm200436t.
A. Nowakowska-Oleksy, J. Soloducho and J. Cabaj, J. Fluoresc., 21, 169 (2011); doi:10.1007/s10895-010-0701-6.
B.C. Raju, K.V. Prasad, G. Saidachary and B. Sridhar, Org. Lett., 16, 420 (2014); doi:10.1021/ol4033122.
I. Thome and C. Bolm, Org. Lett., 14, 1892 (2012); doi:10.1021/ol3005134.
M.C. Reddy, An Improved Process for the Preparation of Antidiabetic Phenoxazine Compounds, WO 2003008397A1 2003 (2003).
J. Jose and K. Burgess, Tetrahedron, 62, 11021 (2006); doi:10.1016/j.tet.2006.08.056.
K. Hayashi, T. Hayashi, K. Miyazawa and A. Tomoda, J. Pharm. Sci., 114, 85 (2010); doi:10.1254/jphs.10027FP.
T. Shimamoto, A. Tomoda, R. Ishida and K. Ohyashiki, Clin. Cancer Res., 7, 704 (2001).
A. Iwata, T. Yamaguchi, K. Sato, N. Yoshitake and A. Tomoda, Biol. Pharm. Bull., 28, 905 (2005); doi:10.1248/bpb.28.905.
M. Idries and A.-M. Abeed, Qua Medicinal J., 4, 120 (2010).
V.H.J. Frade, M.J. Sousa, J.C.V.P. Moura and M.S.T. Gonclaves, 10th International Electronic Conference on Synthetic Organic Chemistry, 1-30 November 2010. http://www.usc.es/congresos/ecsoc/10/ECSCO10.htm.
K. Persson, M. Sc. Thesis, Department of Chemistry, Colorado State University (2012).
K. Kohli, S.K. Srivastava and S.D. Srivastava, J. Applicable Chem., 3, 525 (2014).
J.P. Wolfe and S.L. Buchwald, Org. Khim. Synth. Cok., 10, 423 (2004).
X. Huang, K.W. Anderson, D. Zim, L. Jiang, A. Klapars and S.L. Buchwald, J. Am. Chem. Soc., 125, 6653 (2003); doi:10.1021/ja035483w.
S. Mohanty, D. Suresh, M.S. Balakrishna and J.T. Mague, Tetrahedron, 64, 240 (2008); doi:10.1016/j.tet.2007.10.081.
K.W. Anderson, R.E. Tundel, T. Ikawa, R.A. Altman and S.L. Buchwald, Angew. Chem. Int. Ed., 45, 6523 (2006); doi:10.1002/anie.200601612.