Synthesis and Spectroscopic Characterization of a New Series of Benzo[E][1,3]Oxazepine Compounds from Schiff Bases

  • Hashim J. Azeez Salahaddin University-Erbil
  • Kali M. Qadir Salahaddin University-Erbil
Keywords: Schiff Base, Benzo [e][1, 3] Oxazepine, Antimicrobial Activity

Abstract

The present work includes synthesis, characterization and investigation the biological activity of a new series of benzo [e][1, 3]oxazepine compounds which were prepared from Schiff bases. The synthetic routes have been divided into two steps as follows: The first step includes the synthesis of Schiff bases, by treatment of 4-amino diphenyl amine and different substituted benzaldehydes in absolute ethanol using glacial acetic acid as catalyst. The second step of this work is the synthesis of a series benzo [e][1, 3] oxazepine, by the reaction of the synthesized Schiff bases with phthalic anhydride in dry benzene. The structures of the synthesized products were confirmed on the basis of (UV-Visible, FT-IR, 1H-NMR, 13C-NMR spectroscopy. Some of the synthesized compounds were evaluated for antibacterial activity, against two types of bacteria, Staphylococcus aureus (Gram positive) and Pseudomonas aeruginosa (Gram negative).The results showed the high sensitivity of the synthesized compounds to both types of bacteria.

Author Biographies

Hashim J. Azeez, Salahaddin University-Erbil

Dept. of Chemistry, College of Education, University of Salahaddin - Hawler, Erbil-Kurdistan, Iraq

Kali M. Qadir, Salahaddin University-Erbil

Dept. of Chemistry, College of Education, University of Salahaddin - Hawler, Erbil-Kurdistan, Iraq.

References

Abdelhafez, A. A., and Abdelwahab, B. A. (2008). 5-(4-Chlorophenyl)-5, 6-dihydro-1, 3-oxazepin-7(4H)-one derivative as lipophilic cyclic analogues of baclofen: design, synthesis, and neuropharmacological evaluation. Bioorganic and Medicinal Chemistry, 16(17).p.7983-7991.
Ahmed N. G. and Al-Hashimi H. Y. (2016). Preparation and Characterization of Some New Oxazepine Compounds, Eur. Chem. Bull. 5(3).p. 88-9
Alexander, A. K., Joseph, L., and George, M. (2016). Synthesis of Novel 5, 6 – Benz 1, 3 – Oxazepine 4, 7 – Dione Derivatives and Screening for Antibacterial, Antioxidant and Anti-Inflammatory Activities. European Journal of Pharmaceutical and Medical Research, 3(7).p.330-336.
Aljamali, N.M. (2015).Comparison and Bio-Chemical Study of (Imine, Oxazepam, Diazepam, Sulfide) - Derivatives on Microbial. International Journal of Current Research in Science and Technology, 1(1).p. 9-15.
Hallinan, E. A., Hagen, T. J., Tsymbalov, S., Husa, R. K., Lee, A. C., Stapelfeld, A., and Savage, M. A. (1996). Aminoacetyl moiety as a potential surrogate for diacylhydrazine group of SC-51089, a potent PGE2 antagonist, and its analogs. Journal of Medicinal Chemistry, 39(2).p. 609-613.
Hanoon, H.D. (2011). Synthesis and Characterization of New Seven-Membered Heterocyclic Compounds from Reaction of New Schiff-Bases with Maleic and Phthalic anhydrides. National Journal of Chemistry, 41, p.77- 89.
Hikmet, A., Berat, K., and Fatma, B. (2013). Synthesis and structure-antibacterial activity relationship studies of 4-substituted phenyl-4, 5-Dihidrobenzo[f] [1, 4] oxazepin-3(2H)-thiones. Medicinal Chemistry Research, 20, p.1170-1180.
Kiran, B., Srivastava, V. K. and Ashok, K. (2003). Synthesis of 1, 5-benzothia/oxazepines as potent neuroleptic agents”, Indian Journal of chemistry, 42B, p.1149-1155.
Kubota, K., kurebayashi, H., Miyachi, H., Tobe, M., Onishi, M., and Isobe, Y. (2011). Synthesis and structure-activity relationship of tricyclic carboxylic acids as novel anti-histamines. Bioorganic and Medicinal Chemistry, 19(9).p.3005-3021.
Ren, S., Wang, R., Komastu, K., Bonaz-Krause, P., Zyrianov, Y., Mckenna, C.E., Csipke, C., Tokes, Z.A. and Lein E.J. (2006). Synthesis, biological evaluation, and quantitative structure-activity relationship analysis of new Schiff bases of hydroxysemicarbazide as potential antitumor agents. .J. Med. Chem. 45, p. 410-419.
Serrano-Wu, M. H., Laurent, D. R., Chen, Y., Huang, S., Lam, K. R., Matson, J. A., Mazzucco, C. E., Stickle, T. M., Tully, T. P., Wong, H. S., Vyas, D. M., and Balasubramanian, B. N., (2002). Sordarinoxazepine derivatives as potent antifungal agents. Bioorganic and Medicinal Chemistry Letters, 12(19).p.2757-2760.
Wang, L., Feng, Y., Xue, J. and Li, Y. (2006). Synthesis and characterization of novel pophyrin Schiff bases. J .Serb Chem. Soc. 73, p. 1-6.
Xin-Hua, L., Ying-Ming, J., Bao-An, S., Zhi-Xiang, P., and Song, Y. (2013). Design and synthesis of novel 2-methyl-4,5-substitutedbenzo[f]-3,3a,4,5-tetrahydro-pyrazolo[1,5-d][1,4]oxazepin-8(7H)-one derivatives as telomerase inhibitors. Bioorganic and Medicinal Chemistry Letters, 23(3).p.720-723.
Published
2017-03-30
How to Cite
Azeez, H., & Qadir, K. (2017). Synthesis and Spectroscopic Characterization of a New Series of Benzo[E][1,3]Oxazepine Compounds from Schiff Bases. Science Journal of University of Zakho, 5(1), 101-106. https://doi.org/10.25271/2017.5.1.309
Section
Science Journal of University of Zakho