Synthesis and characterization of new 1,3-Oxazepine-4,7-dione compounds from 1,2-diaminobenzene

https://doi.org/10.53730/ijhs.v6nS4.9123

Authors

  • Miad Hassan Jebur The General Directorate of Education in Najaf Al-Ashraf
  • Elaf Addel Albdere The General Directorate of Education in Babylon
  • Mohammed Kassim Al-Hussainawy The General Directorate of Education in Muthanna
  • Salam Hussein Alwan College of Dentistry, University of Al-Qadisiyah, Diwaniya, Iraq

Keywords:

1,3-oxazepine, Schiff bases synthes, Cyclo addition, biological activity

Abstract

In this research, done synthesized a series of new 1,3-oxazepine-4,7-dione derivatives as D1-D3 compounds via using [2+5] cycloaddition reaction. Synthesized compounds that have been bis azo groups [B1-B3] from 1,2-diaminobenzene via coupling its diazonium salt with phenoxide anion of 4-alkoxybenzaldehyde which Alkoxy was as pentyl, hexyl, and Heptyl groups. These compounds B1-B3 are condensed with 4-Bromoaniline in Schiff bases reactions to give bisazoimine derivatives C1-C3. The compounds C1-C3 were produced by cycloaddition reaction to produce 1,3-oxazepine-4,7-dione derivatives D1-D3. The structures of the synthesized compounds are characterized by spectroscopic methods, such as FTIR, and 1HNMR spectra with the elemental composition analysis. The compounds D1-D3 that are synthesized play a big role in the inhibition of growth.

Downloads

Download data is not yet available.

References

Aftan, M. M., Jabbar, M. Q., Dalaf, A. H., & Salih, H. K. (2021). Application of biological activity of oxazepine and 2-azetidinone compounds and study of their liquid crystalline behavior. Materials Today: Proceedings, 43, 2040–2050.

Alfatlawi, I. O., Sahab, E. H., & Aljamali, N. M. (2018). Synthesis of (Tetrazole, oxazepine, azo, imine) ligands and studying of their (organic identification, chromatography, solubility, physical, thermal analysis, bio-study). Research Journal of Pharmacy and Technology, 11(7), 2821–2828.

Aljamali, N. M. (2015). Review in azo compounds and its biological activity. Biochem Anal Biochem, 4(2), 1–4.

Aryani, L. N. A., & Lesmana, C. B. J. (2019). Neuropsychiatric factor and polymorphism gene in internet addiction. International Journal of Health & Medical Sciences, 2(1), 39-44. https://doi.org/10.31295/ijhms.v2n1.90

Ayfan, A. K. H., Muslim, R. F., & Noori, N. S. (2019). Preparation and Characterization of Novel disubstituted 1, 3-Oxazepine-tetra-one from Schiff bases reaction with 3-methylfuran-2, 5-dione and 3-Phenyldihydrofuran-2, 5-dione. Research Journal of Pharmacy and Technology, 12(3), 1008–1016.

Campiani, G., Nacci, V., Fiorini, I., De Filippis, M. P., Garofalo, A., Greco, G., Novellino, E., Altamura, S., & Di Renzo, L. (1996). Pyrrolobenzothiazepinones and pyrrolobenzoxazepinones: novel and specific non-nucleoside HIV-1 reverse transcriptase inhibitors with antiviral activity. Journal of Medicinal Chemistry, 39(14), 2672–2680.

Carruthers, W. (2013). Cycloaddition reactions in organic synthesis. Elsevier.

De, K., Maity, S., Ghosh, P., & Mukhopadhyay, C. (2019). Na‐Y Zeolite, a convenient and recyclable catalyst for the facile one‐pot synthesis of spiro dibenzo [b, e][1, 4] oxazepine scaffolds. Applied Organometallic Chemistry, 33(6), e4852.

Du, K.-S., & Huang, J.-M. (2019). Electrochemical dehydrogenation of hydrazines to azo compounds. Green Chemistry, 21(7), 1680–1685.

Jabar, S. A., Hussein, A. L., Dalaf, A. H., & Aboud, H. S. (2020). Synthesis and Characterization of Azetidine and Oxazepine Compounds Using Ethyl-4-((4-Bromo Benzylidene) Amino) Benzoate as Precursor and Evalution of Their Biological Activity. Journal of Education and Scientific Studies, 5(16).

Jørgensen, K. A. (2002). Cycloaddition reactions in organic synthesis. John Wiley & Sons.

Kanichar, D., Roppiyakuda, L., Kosmowska, E., Faust, M. A., Tran, K. P., Chow, F., Buglo, E., Groziak, M. P., Sarina, E. A., & Olmstead, M. M. (2014). Synthesis, Characterization, and Antibacterial Activity of Structurally Complex 2‐Acylated 2, 3, 1‐Benzodiazaborines and Related Compounds. Chemistry & Biodiversity, 11(9), 1381–1397.

Kumar, R., & Joshi, Y. C. (2009). Synthesis, antimicrobial and antifungal activities of novel 1H-1, 4-diazepines containing pyrazolopyrimidinone moiety. Journal of Chemical Sciences, 121(4), 497–502.

Mandal, S. M., & Paul, D. (2022). Spectroscopy: Principle, Types and Microbiological Applications. In Automation and Basic Techniques in Medical Microbiology (pp. 49–75). Springer.

Nolte, O., Geitner, R., Hager, M. D., & Schubert, U. S. (2021). IR Spectroscopy as a Method for Online Electrolyte State Assessment in RFBs. Advanced Energy Materials, 11(28), 2100931.

Ozaki, Y., Huck, C., Tsuchikawa, S., & Engelsen, S. B. (2021). Near-Infrared Spectroscopy: Theory, Spectral Analysis, Instrumentation, and Applications. Springer.

Prakash, S., Somiya, G., Elavarasan, N., Subashini, K., Kanaga, S., Dhandapani, R., Sivanandam, M., Kumaradhas, P., Thirunavukkarasu, C., & Sujatha, V. (2021). Synthesis and characterization of novel bioactive azo compounds fused with benzothiazole and their versatile biological applications. Journal of Molecular Structure, 1224, 129016.

Roduner, E., Krüger, T., Forbes, P., & Kress, K. (2019). Optical Spectroscopy: Fundamentals and Advanced Applications. World Scientific.

Sallal, Z. A., & Ghanem, H. T. (2018). Synthesis and Identification of New Oxazepine Derivatives bearing Azo group in their structures. Iraqi Journal of Science, 1–8.

Scimeca, M., Bischetti, S., Lamsira, H. K., Bonfiglio, R., & Bonanno, E. (2018). Energy Dispersive X-ray (EDX) microanalysis: A powerful tool in biomedical research and diagnosis. European Journal of Histochemistry: EJH, 62(1).

Sharma, G., Park, J. Y., & Park, M. S. (2008). Design and synthesis of 6-amino-1, 4-oxazepane-3, 5-dione derivatives as novel broad spectrum anticonvulsants. Bioorganic & Medicinal Chemistry Letters, 18(11), 3188–3191.

Sleevi, M. C., Cale Jr, A. D., Gero, T. W., Jaques, L. W., Welstead, W. J., Johnson, A. F., Kilpatrick, B. F., Demian, I., Nolan, J. C., & Jenkins, H. (1991). Optical isomers of rocastine and close analogs: synthesis and H1 antihistaminic activity of its enantiomers and their structural relationship to the classical antihistamines. Journal of Medicinal Chemistry, 34(4), 1314–1328.

Widana, I.K., Sumetri, N.W., Sutapa, I.K., Suryasa, W. (2021). Anthropometric measures for better cardiovascular and musculoskeletal health. Computer Applications in Engineering Education, 29(3), 550–561. https://doi.org/10.1002/cae.22202

Xie, J., Lee, J. Y., & Wang, D. I. C. (2007). Synthesis of single-crystalline gold nanoplates in aqueous solutions through biomineralization by serum albumin protein. The Journal of Physical Chemistry C, 111(28), 10226–10232.

Ye, X., Chen, Y., Ling, C., Ding, R., Wang, X., Zhang, X., & Chen, S. (2018). One-pot synthesis of Schiff base compounds via photocatalytic reaction in the coupled system of aromatic alcohols and nitrobenzene using CdIn 2 S 4 photocatalyst. Dalton Transactions, 47(32), 10915–10924.

Zhang, F., Chen, Z., Cheung, C. W., & Ma, J. (2020). Aryl Diazonium Salt‐Triggered Cyclization and Cycloaddition Reactions: Past, Present, and Future. Chinese Journal of Chemistry, 38(10), 1132–1152.

Published

17-06-2022

How to Cite

Jebur, M. H., Albdere, E. A., Al-Hussainawy, M. K., & Alwan, S. H. (2022). Synthesis and characterization of new 1,3-Oxazepine-4,7-dione compounds from 1,2-diaminobenzene. International Journal of Health Sciences, 6(S4), 4578–4589. https://doi.org/10.53730/ijhs.v6nS4.9123

Issue

Section

Peer Review Articles