Synthesis of Highly Functionalized Angular Azaphenoxazines and Related Benzo Analogues via Suzuki-Miyaura Cross-Coupling Reaction

U.C. Okoro; M.A. Ezeokonkwo; E.A. Ujah; R.N. Nweloke

doi:10.14233/ajchem.2016.19299

Issue

Vol. 28 No. 2 (2016): Vol 28 Issue 2

Issue Published : November 3, 2015

This work is licensed under a Creative Commons Attribution 4.0 International License.

Synthesis of Highly Functionalized Angular Azaphenoxazines and Related Benzo Analogues via Suzuki-Miyaura Cross-Coupling Reaction

https://doi.org/10.14233/ajchem.2016.19299

U.C. Okoro

Department of Pure and Industrial Chemistry, University of Nigeria, Nsukka 410002, Nigeria

M.A. Ezeokonkwo

Department of Pure and Industrial Chemistry, University of Nigeria, Nsukka 410002, Nigeria

E.A. Ujah

Department of Pure and Industrial Chemistry, University of Nigeria, Nsukka 410002, Nigeria

R.N. Nweloke

Department of Pure and Industrial Chemistry, University of Nigeria, Nsukka 410002, Nigeria

Corresponding Author(s) : M.A. Ezeokonkwo

mercy.ezeokonkwo@unn.edu.ng

Asian Journal of Chemistry, Vol. 28 No. 2 (2016): Vol 28 Issue 2
Article Published : November 3, 2015

Abstract

Highly functionalized angular azaphenoxazines and the benzo analogues have been prepared following the Suzuki-Miyaura protocol, which consists in the palladium catalyzed coupling of 11-amino-6-chloro-8,10-diazabenzo[a]phenoxazin-5-one, 6-chloro-11-azabenzo[a]phenoxazin-5-one, 6-chlorobenzo[a]phenoxazin-5-one and 6-chlorodibenzo[a,j]phenoxazin-5-one respectively with various boronic acids at 110 °C in DMF-toluene. The corresponding products were obtained in trace to excellent yields in the presence of piperazine ligand and K₂CO₃ as base. The structures of the newly synthesized compounds were established by spectral analysis.

Keywords

Azaphenoxazines Benzo analogues Palladium catalyzed coupling Suzuki-Miyaura cross-coupling Boronic acids

Okoro, U., Ezeokonkwo, M., Ujah, E., & Nweloke, R. (2015). Synthesis of Highly Functionalized Angular Azaphenoxazines and Related Benzo Analogues via Suzuki-Miyaura Cross-Coupling Reaction. Asian Journal of Chemistry, 28(2), 317–324. https://doi.org/10.14233/ajchem.2016.19299

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References

A.V. Samet, K.A. Kislyi, V.N. Marshalkin and V.V. Semenov, Izv. Ross. Akad. Nauk. Ser. Khim., 529 (2006).
T. Shimamaoto, A. Tomoda, R. Ishida and K. Ohyashiki, Am. Assoc. Cancer Res., 7, 704 (2001).
J.K. Horton, K.N. Thimmaiah, F.C. Harwood, J.F. Kuttesch and P.J. Houghton, Mol. Pharmacol. Abstr., 44, 552 (1993).
T.U.S. Chu-Daniel, Chem. Abstr., 104, 109663K (1986).
B. Boothroyd and E.R. Clark, J. Chem. Soc., 1499 (1953); doi:10.1039/JR9530001499.
S. Kapur and R. McClelland, US Patent 6,890,919 (2005).
H. Maas, A. Khatyr and G. Calzaferri, Micropor. Mesopor. Mater., 65, 233 (2003); doi:10.1016/j.micromeso.2003.08.014.
G.B. Eregowda, B.C. Channu, S. Jagadeesh, H.N. Kalpana, R. Hegde and K.N. Thimmaiah, Indian J. Chem., 39B, 243 (2000).
C.O. Okafor, Phosphorus Sulfur Silicon Rel. Elem., 4, 79 (1978); doi:10.1080/03086647808079968.
M.S. Newman and C.Y. Perry, J. Org. Chem., 28, 116 (1963); doi:10.1021/jo01036a026.
N. Miyaura and A. Suzuki, Chem. Rev., 95, 2457 (1995); doi:10.1021/cr00039a007.
S.P. Stanforth, Tetrahedron, 54, 263 (1998); doi:10.1016/S0040-4020(97)10233-2.
L. Kurti and B. Czako, Elsevier Academic Press Burlington, USA, pp. 448 (2005).
J.W. Moore, J. Chem. Educ., 78, 7 (2001); doi:10.1021/ed078p7.
N. Miyuara, in ed.: L.S. Libeskind, Advances in Metal-Organic Chemistry, London, p. 187 (1998).
R. Martin and S.L. Buchwald, Acc. Chem. Res., 41, 1461 (2008); doi:10.1021/ar800036s.
S. Kotha, K. Lahiri and D. Kashinath, Tetrahedron, 58, 9633 (2002); doi:10.1016/S0040-4020(02)01188-2.
S. Brase and A. Meijere, in eds.: E. Diederich and P.J. Stang, Metal-Catalyzed Cross-Coupling Reactions, Chapters 3 & 6, Wiley, New York (1998).
M. Sasaki and H. Fuwa, Synlett, 1851 (2004); doi:10.1055/s-2004-830860.
T.R. Burke, D.G. Liu and Y. Gao, J. Org. Chem., 65, 6288 (2000); doi:10.1021/jo000643x.
J.P. Wolfe, R.A. Singer, B.H. Yang and S.L. Buchwald, J. Am. Chem. Soc., 121, 9550 (1999); doi:10.1021/ja992130h.
A.W. Franz and T.J.J. Muller, Synthesis, 1121 (2008); doi:10.1055/s-2008-1032118.
S. Mohanty, D. Suresh, M.S. Balakrishna and J.T. Mague, Tetrahedron, 64, 240 (2008); doi:10.1016/j.tet.2007.10.081.
C.O. Okafor, Dyes Pigments, 7, 103 (1986); doi:10.1016/0143-7208(86)85003-3.
C.O. Okafor, I.O. Okerulu and S.I. Okeke, Dyes Pigments, 8, 11 (1987); doi:10.1016/0143-7208(87)85002-7.
I.L. Finar, The Fundamental Principles of Organic Chemistry, Longman Group Ltd., London, edn 6, Vol. 1, p. 868 (2007).

References

A.V. Samet, K.A. Kislyi, V.N. Marshalkin and V.V. Semenov, Izv. Ross. Akad. Nauk. Ser. Khim., 529 (2006).

T. Shimamaoto, A. Tomoda, R. Ishida and K. Ohyashiki, Am. Assoc. Cancer Res., 7, 704 (2001).

J.K. Horton, K.N. Thimmaiah, F.C. Harwood, J.F. Kuttesch and P.J. Houghton, Mol. Pharmacol. Abstr., 44, 552 (1993).

T.U.S. Chu-Daniel, Chem. Abstr., 104, 109663K (1986).

B. Boothroyd and E.R. Clark, J. Chem. Soc., 1499 (1953); doi:10.1039/JR9530001499.

S. Kapur and R. McClelland, US Patent 6,890,919 (2005).

H. Maas, A. Khatyr and G. Calzaferri, Micropor. Mesopor. Mater., 65, 233 (2003); doi:10.1016/j.micromeso.2003.08.014.

G.B. Eregowda, B.C. Channu, S. Jagadeesh, H.N. Kalpana, R. Hegde and K.N. Thimmaiah, Indian J. Chem., 39B, 243 (2000).

C.O. Okafor, Phosphorus Sulfur Silicon Rel. Elem., 4, 79 (1978); doi:10.1080/03086647808079968.

M.S. Newman and C.Y. Perry, J. Org. Chem., 28, 116 (1963); doi:10.1021/jo01036a026.

N. Miyaura and A. Suzuki, Chem. Rev., 95, 2457 (1995); doi:10.1021/cr00039a007.

S.P. Stanforth, Tetrahedron, 54, 263 (1998); doi:10.1016/S0040-4020(97)10233-2.

L. Kurti and B. Czako, Elsevier Academic Press Burlington, USA, pp. 448 (2005).

J.W. Moore, J. Chem. Educ., 78, 7 (2001); doi:10.1021/ed078p7.

N. Miyuara, in ed.: L.S. Libeskind, Advances in Metal-Organic Chemistry, London, p. 187 (1998).

R. Martin and S.L. Buchwald, Acc. Chem. Res., 41, 1461 (2008); doi:10.1021/ar800036s.

S. Kotha, K. Lahiri and D. Kashinath, Tetrahedron, 58, 9633 (2002); doi:10.1016/S0040-4020(02)01188-2.

S. Brase and A. Meijere, in eds.: E. Diederich and P.J. Stang, Metal-Catalyzed Cross-Coupling Reactions, Chapters 3 & 6, Wiley, New York (1998).

M. Sasaki and H. Fuwa, Synlett, 1851 (2004); doi:10.1055/s-2004-830860.

T.R. Burke, D.G. Liu and Y. Gao, J. Org. Chem., 65, 6288 (2000); doi:10.1021/jo000643x.

J.P. Wolfe, R.A. Singer, B.H. Yang and S.L. Buchwald, J. Am. Chem. Soc., 121, 9550 (1999); doi:10.1021/ja992130h.

A.W. Franz and T.J.J. Muller, Synthesis, 1121 (2008); doi:10.1055/s-2008-1032118.

S. Mohanty, D. Suresh, M.S. Balakrishna and J.T. Mague, Tetrahedron, 64, 240 (2008); doi:10.1016/j.tet.2007.10.081.

C.O. Okafor, Dyes Pigments, 7, 103 (1986); doi:10.1016/0143-7208(86)85003-3.

C.O. Okafor, I.O. Okerulu and S.I. Okeke, Dyes Pigments, 8, 11 (1987); doi:10.1016/0143-7208(87)85002-7.

I.L. Finar, The Fundamental Principles of Organic Chemistry, Longman Group Ltd., London, edn 6, Vol. 1, p. 868 (2007).

Issue

Vol. 28 No. 2 (2016): Vol 28 Issue 2

Synthesis of Highly Functionalized Angular Azaphenoxazines and Related Benzo Analogues via Suzuki-Miyaura Cross-Coupling Reaction

Corresponding Author(s) : M.A. Ezeokonkwo

Abstract

Keywords

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