Synthesis and Characterization of New 3,4-Dihydro-2H-benzo- and Naphtho-1,3-oxazine Derivatives

A.U. Garin Gabbas; M.B. Ahmad; N. Zainuddin; N.A. Ibrahim

doi:10.14233/ajchem.2016.19666

Issue

Vol. 28 No. 6 (2016): Vol 28 Issue 6

Issue Published : February 29, 2016

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

Synthesis and Characterization of New 3,4-Dihydro-2H-benzo- and Naphtho-1,3-oxazine Derivatives

https://doi.org/10.14233/ajchem.2016.19666

A.U. Garin Gabbas

Department of Chemistry, Faculty of Science, Universiti Putra Malaysia, 43400 Serdang, Selangor, Malaysia

M.B. Ahmad

Department of Chemistry, Faculty of Science, Universiti Putra Malaysia, 43400 Serdang, Selangor, Malaysia

N. Zainuddin

Department of Chemistry, Faculty of Science, Universiti Putra Malaysia, 43400 Serdang, Selangor, Malaysia

N.A. Ibrahim

Department of Chemistry, Faculty of Science, Universiti Putra Malaysia, 43400 Serdang, Selangor, Malaysia

Corresponding Author(s) : M.B. Ahmad

mansorahmad@upm.edu.my

Asian Journal of Chemistry, Vol. 28 No. 6 (2016): Vol 28 Issue 6
Article Published : February 29, 2016

Abstract

New 1,3-benzoxazine and naphthoxazine monomers were synthesized using a modified step-wise technique in which formaldehyde was replaced with methylene bromide for ring-closure reaction in the last synthetic step. Salicylaldehyde and 2-hydroxy-1-naphthaldehyde were used as the aromatic aldehydes and 4-fluoroaniline, 4-butylaniline, hexamethylenediamine, p-phenylenediamine and 2-aminothiazole were used as the primary amines. Condensation of the aromatic aldehydes and the aromatic primary amines in absolute ethanol gives imine compounds which on reduction with sodium borohydride in methanol give 2-hydroxybenzylamines/2-hydroxynaphthylamines. Ring-closure reaction between 2-hydroxybenzylamines/2-hydroxynaphthylamines and methylene bromide in absolute ethanol gives the 1,3-benzoxazines and naphthoxazines in good yields. The structures of the new 1,3-benzoxazine and naphthoxazine monomers were confirmed by FT-IR, ¹H NMR and ¹³C NMR spectral analysis, Mass spectroscopy (GC-MS) and elemental analysis. The mass spectrum of the synthesized compounds showed molecular ion peaks centered at m/z 229, 218, 316, 317, 444 and 268 which are equivalent to the molecular weights of the new synthesized compounds a, b, c, d, e and f, respectively. Results of elemental analysis also confirm the calculated result to be in agreement with the experimental result.

Keywords

1,3-Benzoxazines 1,3-Naphthoxazines Methylene bromide Characterization Modified step-wise process

Garin Gabbas, A., Ahmad, M., Zainuddin, N., & Ibrahim, N. (2016). Synthesis and Characterization of New 3,4-Dihydro-2H-benzo- and Naphtho-1,3-oxazine Derivatives. Asian Journal of Chemistry, 28(6), 1304–1306. https://doi.org/10.14233/ajchem.2016.19666

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W.J. Burke, J. Am. Chem. Soc., 71, 609 (1949); doi:10.1021/ja01170a063.

W.J. Burke, M.J. Kolbezen and C.W. Stephens, J. Am. Chem. Soc., 74, 3601 (1952); doi:10.1021/ja01134a039.

W.J. Burke, K.C. Murdock and G. Ec, J. Am. Chem. Soc., 76, 1677 (1954); doi:10.1021/ja01635a065.

K.D. Demir, B. Kiskan, B. Aydogan and Y. Yagci, React. Funct. Polym., 73, 346 (2013); doi:10.1016/j.reactfunctpolym.2012.04.016.

H. Ishida and T. Agag, Handbook of Benzoxazine Resins, Elsevier, Amsterdam, p. 3 (2011).

B. Kiskan, B. Koz and Y. Yagci, J. Polym. Sci. A Polym. Chem., 47, 6955 (2009); doi:10.1002/pola.23735.

Y. Liu, S. Zhao, H. Zhang, M. Wang and M. Run, Thermochim. Acta, 549, 42 (2012); doi:10.1016/j.tca.2012.09.017.

N. Siddiqui, R. Ali, M.S. Alam and W. Ahsan, J. Chem. Pharm. Res., 2, 309 (2010).

R. Andreu, J.A. Reina and J.C. Ronda, J. Polym. Sci. A Polym. Chem., 46, 3353 (2008); doi:10.1002/pola.22677.

A. Chernykh, T. Agag and H. Ishida, Polymer, 50, 3153 (2009); doi:10.1016/j.polymer.2009.04.061.

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

Y.-H. Wang, C.-M. Chang and Y.-L. Liu, Polymer, 53, 106 (2012); doi:10.1016/j.polymer.2011.11.040.

S.F. Li, H. Wang and M. Tao, Desig. Monomers Polym., 17, 693 (2014); doi:10.1080/15685551.2014.907625.

K. Zhang and H. Ishida, Frontiers Mater., 2, 1 (2015); doi:10.3389/fmats.2015.00005.

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B.P. Mathew, A. Kumar, S. Sharma, P.K. Shukla and M. Nath, Eur. J. Med. Chem., 45, 1502 (2010); doi:10.1016/j.ejmech.2009.12.058.

Z. Tang, Z. Zhu, L. Yan, S. Chang and H. Liu, J. Heterocycl. Chem., 50, 1116 (2013); doi:10.1002/jhet.1590.

J. Wang, X. Fang, M. Wu, X. He, W. Liu and X. Shen, Eur. Polym. J., 47, 2158 (2011); doi:10.1016/j.eurpolymj.2011.08.005.

M. Imran, B. Kiskan and Y. Yagci, Tetrahedron Lett., 54, 4966 (2013); doi:10.1016/j.tetlet.2013.07.041.

H.F. Anwar, L. Skattebøl and T.V. Hansen, Tetrahedron, 63, 9997 (2007); doi:10.1016/j.tet.2007.07.064.

R.J. Lewis Sr., Hazardous Chemicals Desk Reference, John Wiley & Sons, New York, p. 782 (2008).

R. Andreu and J.C. Ronda, Synth. Commun., 38, 2316 (2008); doi:10.1080/00397910802138629.

Issue

Vol. 28 No. 6 (2016): Vol 28 Issue 6

Synthesis and Characterization of New 3,4-Dihydro-2H-benzo- and Naphtho-1,3-oxazine Derivatives

Corresponding Author(s) : M.B. Ahmad

Abstract

Keywords

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