One-Pot Synthesis of Benzoxazines Through Mannich Condensations

Rajib Kumar Debnath; Apurba Kalita; Biplab Mondal; Jatindra Nath Ganguli

doi:10.14233/ajchem.2014.16479

Issue

Vol. 26 No. 19 (2014): Vol 26 Issue 19

Issue Published : September 16, 2014

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

One-Pot Synthesis of Benzoxazines Through Mannich Condensations

https://doi.org/10.14233/ajchem.2014.16479

Rajib Kumar Debnath

Department of Chemistry, Guwahati University, Guwahati-781 014, India

Apurba Kalita

Department of Chemistry, Indian Institute of Technology Guwahati-781 039, India

Biplab Mondal

Department of Chemistry, Indian Institute of Technology Guwahati-781 039, India

Jatindra Nath Ganguli

Department of Chemistry, Guwahati University, Guwahati-781 014, India

Corresponding Author(s) : Jatindra Nath Ganguli

rkdn1981@gmail.com

Asian Journal of Chemistry, Vol. 26 No. 19 (2014): Vol 26 Issue 19
Article Published : September 18, 2014

Abstract

Five benzoxazine were synthesized by Mannich condensation reaction between 2,4-ditert-butyl phenol, formaldehyde and different amines in one pot synthesis. The benzoxazines were characterized by elemental analysis, spectral and crystal structure determination. The synthesis process requires considerable less time and three of the five benzoxazines are new and reported for the first time.

Keywords

Benzoxazines Formaldehyde Different amines 2,4-Ditert-butyl phenol Mannich reaction

Kumar Debnath, R., Kalita, A., Mondal, B., & Nath Ganguli, J. (2014). One-Pot Synthesis of Benzoxazines Through Mannich Condensations. Asian Journal of Chemistry, 26(19), 6519–6522. https://doi.org/10.14233/ajchem.2014.16479

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References

A. Novelli and P. Adams, J. Am. Chem. Soc., 59, 2259 (1937); doi:10.1021/ja01290a043.
(a) T. Urbanski and S. Slopek, Nature, 168, 262 (1951); doi:10.1038/168262d0; (b) E.S. Lane, Brit. Patent, 694,489 (1953); (c) T. Shono and A. Takahashi, J. Chem. Soc. Japan, 57, 569 (1954); (d) J.B. Chylinska, T. Urbanski and M. Mordarski, J. Med. Chem., 6, 484 (1963); doi:10.1021/jm00341a004.
S.M. Bromidge, B. Bertani, M. Borriello, A. Bozzoli, S. Faedo, M. Gianotti, L.J. Gordon, M. Hill, V. Zucchelli, J.M. Watson and L. Zonzini, Bioorg. Med. Chem. Lett., 19, 2338 (2009); doi:10.1016/j.bmcl.2009.02.056.
J.C. Kern, E.A. Terefenko, A. Fensome, R. Unwallla, J. Wrobel, Y. Zhu, J. Cohen, R. Winneker, Z. Zhang and P. Zhang, Bioorg. Med. Chem. Lett., 17, 189 (2007); doi:10.1016/j.bmcl.2006.09.060.
S.J. Hays, B.W. Caprathe, J.L. Gilmore, N. Amin, M.R. Emmerling, W. Michael, R. Nadimpalli, R. Nath, K.J. Raser, D. Stafford, D. Watson, K. Wang and J.C. Jaen, J. Med. Chem., 41, 1060 (1998); doi:10.1021/jm970394d.
A. Nakagawa, S. Uno, M. Makishima, H. Miyachi and Y. Hashimoto, Bioorg. Med. Chem., 16, 7046 (2008); doi:10.1016/j.bmc.2008.05.016.
N.N. Ghosh, B. Kiskan and Y. Yagci, Prog. Polym. Sci., 32, 1344 (2007); doi:10.1016/j.progpolymsci.2007.07.002.
T. Agag, L. Jin and H. Ishida, Polymer, 50, 5940 (2009); doi:10.1016/j.polymer.2009.06.038.
M. Heydenreich, A. Koch, S. Klod, I. Szatmari, F. Fulop and E. Kleinpeter, Tetrahedron, 62, 11081 (2006); doi:10.1016/j.tet.2006.09.037.
I. Szatmari, T.A. Martinek, L. Lazar and F. Fulop, Tetrahedron, 59, 2877 (2003); doi:10.1016/S0040-4020(03)00331-4.
I. Szatmari, T.A. Martinek, L. Lazar, A. Koch, E. Kleinpeter, K. Neuvonen and F. Fulop, J. Org. Chem., 69, 3645 (2004); doi:10.1021/jo0355810.
K. Kobayashi, Y. Yokoi, T. Komatsu and H. Konishi, Tetrahedron, 66, 9336 (2010); doi:10.1016/j.tet.2010.10.010.
S. Ma, J. Li, Y. Sun, J. Zhao, X. Zhao, X. Yang, L. Zhang, L. Wang and Z. Zhou, Tetrahedron, 62, 7999 (2006); doi:10.1016/j.tet.2006.06.033.
C. Cimarelli, A. Mazzanti, G. Palmieri and E. Volpini, J. Org. Chem., 66, 4759 (2001); doi:10.1021/jo0101205.
K. Kobayashi, H. Hashimoto, Y. Kanbe and H. Konishi, Tetrahedron, 67, 4535 (2011); doi:10.1016/j.tet.2011.04.088.
C. Theeraladanon, M. Arisawa, A. Nishida and M. Nakagawa, Tetrahedron, 60, 3017 (2004); doi:10.1016/j.tet.2004.01.084.
K. Kobayashi, A. Takanohashi, K. Hashimoto, O. Morikawa and H. Konishi, Tetrahedron, 62, 3158 (2006); doi:10.1016/j.tet.2005.11.078.
W.J. Burke, E.L.M. Glennie and C. Weatherbee, J. Org. Chem., 29, 909 (1964); doi:10.1021/jo01027a038.
R.K. Debnath, A. Kalita, P. Kumar, B. Mondal and J.N. Ganguli, Polyhedron, 51, 222 (2013); doi:10.1016/j.poly.2012.12.036.
CCDC, 837284 & 837285 Contains the Supplementary Crystallographic Data for this Compound. These Data can be Obtained free of Charge from the Cambridge Crystallographic Data Center via www.ccdc.cam.ac.uk/data_request/cif.

References

A. Novelli and P. Adams, J. Am. Chem. Soc., 59, 2259 (1937); doi:10.1021/ja01290a043.

(a) T. Urbanski and S. Slopek, Nature, 168, 262 (1951); doi:10.1038/168262d0; (b) E.S. Lane, Brit. Patent, 694,489 (1953); (c) T. Shono and A. Takahashi, J. Chem. Soc. Japan, 57, 569 (1954); (d) J.B. Chylinska, T. Urbanski and M. Mordarski, J. Med. Chem., 6, 484 (1963); doi:10.1021/jm00341a004.

S.M. Bromidge, B. Bertani, M. Borriello, A. Bozzoli, S. Faedo, M. Gianotti, L.J. Gordon, M. Hill, V. Zucchelli, J.M. Watson and L. Zonzini, Bioorg. Med. Chem. Lett., 19, 2338 (2009); doi:10.1016/j.bmcl.2009.02.056.

J.C. Kern, E.A. Terefenko, A. Fensome, R. Unwallla, J. Wrobel, Y. Zhu, J. Cohen, R. Winneker, Z. Zhang and P. Zhang, Bioorg. Med. Chem. Lett., 17, 189 (2007); doi:10.1016/j.bmcl.2006.09.060.

S.J. Hays, B.W. Caprathe, J.L. Gilmore, N. Amin, M.R. Emmerling, W. Michael, R. Nadimpalli, R. Nath, K.J. Raser, D. Stafford, D. Watson, K. Wang and J.C. Jaen, J. Med. Chem., 41, 1060 (1998); doi:10.1021/jm970394d.

A. Nakagawa, S. Uno, M. Makishima, H. Miyachi and Y. Hashimoto, Bioorg. Med. Chem., 16, 7046 (2008); doi:10.1016/j.bmc.2008.05.016.

N.N. Ghosh, B. Kiskan and Y. Yagci, Prog. Polym. Sci., 32, 1344 (2007); doi:10.1016/j.progpolymsci.2007.07.002.

T. Agag, L. Jin and H. Ishida, Polymer, 50, 5940 (2009); doi:10.1016/j.polymer.2009.06.038.

M. Heydenreich, A. Koch, S. Klod, I. Szatmari, F. Fulop and E. Kleinpeter, Tetrahedron, 62, 11081 (2006); doi:10.1016/j.tet.2006.09.037.

I. Szatmari, T.A. Martinek, L. Lazar and F. Fulop, Tetrahedron, 59, 2877 (2003); doi:10.1016/S0040-4020(03)00331-4.

I. Szatmari, T.A. Martinek, L. Lazar, A. Koch, E. Kleinpeter, K. Neuvonen and F. Fulop, J. Org. Chem., 69, 3645 (2004); doi:10.1021/jo0355810.

K. Kobayashi, Y. Yokoi, T. Komatsu and H. Konishi, Tetrahedron, 66, 9336 (2010); doi:10.1016/j.tet.2010.10.010.

S. Ma, J. Li, Y. Sun, J. Zhao, X. Zhao, X. Yang, L. Zhang, L. Wang and Z. Zhou, Tetrahedron, 62, 7999 (2006); doi:10.1016/j.tet.2006.06.033.

C. Cimarelli, A. Mazzanti, G. Palmieri and E. Volpini, J. Org. Chem., 66, 4759 (2001); doi:10.1021/jo0101205.

K. Kobayashi, H. Hashimoto, Y. Kanbe and H. Konishi, Tetrahedron, 67, 4535 (2011); doi:10.1016/j.tet.2011.04.088.

C. Theeraladanon, M. Arisawa, A. Nishida and M. Nakagawa, Tetrahedron, 60, 3017 (2004); doi:10.1016/j.tet.2004.01.084.

K. Kobayashi, A. Takanohashi, K. Hashimoto, O. Morikawa and H. Konishi, Tetrahedron, 62, 3158 (2006); doi:10.1016/j.tet.2005.11.078.

W.J. Burke, E.L.M. Glennie and C. Weatherbee, J. Org. Chem., 29, 909 (1964); doi:10.1021/jo01027a038.

R.K. Debnath, A. Kalita, P. Kumar, B. Mondal and J.N. Ganguli, Polyhedron, 51, 222 (2013); doi:10.1016/j.poly.2012.12.036.

CCDC, 837284 & 837285 Contains the Supplementary Crystallographic Data for this Compound. These Data can be Obtained free of Charge from the Cambridge Crystallographic Data Center via www.ccdc.cam.ac.uk/data_request/cif.

Issue

Vol. 26 No. 19 (2014): Vol 26 Issue 19

One-Pot Synthesis of Benzoxazines Through Mannich Condensations

Corresponding Author(s) : Jatindra Nath Ganguli

Abstract

Keywords

Full Article

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