Synthesis, Identification and Biological Activity of New Heterocyclic Compounds from Reaction of New Schiff-Bases with Phathalic Anhydride
DOI:
https://doi.org/10.25271/sjuoz.2020.8.1.641Keywords:
Oxazepine, Schiff bases, 1, 7-diaminoheptane, 1, 8-diaminooctane, Antibacterial activity, phathalic anhydrideAbstract
Series of new Schiff bases and their derivatives (Oxazepine) have been synthesized during two steps. The first step synthesis of imines derivatives (1-10) by the condensation reaction of 1, 7-diaminohepatane and 1,8-diaminooctane with different substituted aromatic aldehydes by using glacial acetic acid as catalyst. The second step includes reaction of the prepared Schiff bases derivatives with phathalic anhydride in dry benzene to obtain seven-membered heterocyclic ring derivatives (11-15). The biological activities of some prepared compounds were also studied against different kinds of bacteria. The new derivatives were confirmed by suing a range of experimental techniques including 1HNMR, 13C NMR, IR and Mass spectra.
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Z. H. Abood, ''Using A pericyclic Reactions for The Synthesis of New 1, 3-Oxazepine Compounds From New Imines,'' Journal of Kerbala University, vol. 8(1), pp. 354-370, 2010.
Z. H. Abood, R. T. Haiwal, H. T. ghanin, S. M. Radhi, ''Synthesis of Some New Schiff Bases, Tetrazole and 1,3-Oxazepine Derivatives Containing Azo Group and 1,3,4- Thiadiazole Moiety,'' Journal of Babylon University/Pure and Applied Sciences, vol. 21(1), pp. 181-205, 2013.
A. Hameed,''Microwave Synthesis of Some New 1,3-Oxazepine Compounds as Photostabilizing Additives for Pmma Films'', Journal of Al-Nahrain University, vol. 15, pp. 47-59, 2012.
A. A. Abedel-Hahez, and B. A. Abdel-Wahab,''5-(4-Chlorophenyl)-5,6-dihydro-1,3-oxazepin-7(4H)-one Derivatives as Lipophilic Cyclic Analogues of Baclofen: Design, Synthesis, and Neuropharmacological Evaluation'', Bioorganic & Medicinal Chemistry, vol. 16, pp. 7983-7991, 2008
C. Celik, M. Aslantas E. Sahin, A, Kayraldiz, and M. Tumer, ''Structural characterization, genotoxicity and electrochemical properties of the Schiff base ligands and their Ni(II) complexe'', J. of Optoelectronics and Advanced Materals'', vol. 11(10), pp. 1404, 2009.
E. A. Hallinan, T. J. Hagen, S. Tsymbalov, R. K, Husa, A. C. Lee, A. Stapelfeld, and M. A. Savage,'' Aminoacetyl Moiety as a Potential Surrogate for Diacylhydrazine Group of SC-51089, a Potent PGE2 Antagonist, and Its Analogs'', Journal of Medicinal Chemistry, vol. 39, pp. 609-613, 1996.
H. D. Hanoon, ''Synthesis and Characterization of New Sevev-Membered Heterocyclic Compounds from Reaction of New Schiff Bases with Maleic and Phthalic Anhydrides'', National Journal of Chemistry, vol. 41, pp. 77-89, 2011.
H. M. Sadiq, ''Synthesis and Characterization of Novel 1,3-Oxazepine Derivatives from Aminopyrazine'', World Journal of Pharmacy and Pharmaceutical Sciences, vol. 6(5), pp. 186-198, 2017.
H. Agirbas, B. Kemal, and F. Budak, ''Synthesis and Structure-Antibacterial Activity Relationship Studies of 4-Substituted phenyl-4, 5-dihydrobenzo[f][1,4]- oxazepin-3(2H)-thiones'', Medicinal Chemistry Research, vol. 20, pp. 1170-1180, 2011.
J. H. Abdul-wahid, A S. Hameed, and A. K. Mohammed, ''Synthesis Characterization of Some New Heterocyclic Compounds Containing1, 3-Oxazepine Ring'', Kirkuk University Journal /Scientific Studies, vol. 11(3), pp. 237-247, 2016.
K. F. Hamak, and H. H. Eissa, ''Synthesis, Characterization, Biological Evaluation and AntiCorrosion Activity of Some Heterocyclic Compounds Oxazepine Derivatives from Schiff Bases'', Organic Chem Curr Res, vol. 2(3), pp. 1-7, 2013.
K. Kubota, H. Kurebayashi, H. Miyachi, M. Tobe, M. Onishi, and Y. Isobe, ''Synthesis and Structure-Activity Relationship of Tricyclic Carboxylic Acid as Novel Anti-Histamines'', Bioorganic & Medicinal Chemistry, vol. 19, pp. 3005-3021, 2011.
K. Bajajt, V. K. Srivastava, and A. Kumar, ''Synthesis of 1, 5-Benzothia/Oxazepine as Potent Neuroleptic Agents'', Indian Journal of Chemistry. Section B: Organic Chemistry, Including Medical Chemistry, vol. 42, pp. 1149-1155, 2003.
L. M. Prescott, J. P. Harley, and D. A. Klein, Microbiology”, 3rd ed. Brown Publisher, London; 1996.
M. J. Al-Jeboori, and A. H. Dawood, ''Synthesis and Structural Studies of Novel 2,6-Diformyl-p-Cresol Bis-(thiosemicarbazone) Ligand and Their Binuclear Complexes with Ni+2, Pd+2, Zn+2, Cd+2 and Hg+2 Metal Ions,'' Journal of Kerbala University, vol. 6(1), pp. 268, 2008.
M. T. Khattar, N. M. Aljamali, and K. K. Alasadi, ''Synthesis of Heterocyclic Compounds from Imine and Study of Chromatography Applications,'' Asian J. Research Chem, vol. 7(8), pp. 734-747. 2004.
M. N. Abdullah, J. B. Ziwar, and N. Y. Musheer, ''Synthesis of some Heterocyclic Compounds (Oxazepine, Diazepine) using Ultrasound Irradiation,'' ZANCO Journal of Pure and Applied Sciences, vol. 28(2), pp. 235-239, 2016.
M. H. Serrano-Wu, D. R. St. Laurent, Y. Chen, S. Huang, K. R. Lam, et al, ''Sordarin Oxazepine Derivatives as Potent Antifungal Agents,'' Bioorganic & Medicinal Chemistry Letters, vol. 12, pp. 2757-2760, 2002.
N. A. Saeed, Ph.D. Thesis, Al-Nahrain University, 2005.
N. M. Aljamali, K. J. Ali, N. S. Salih, and S. H. Ridha, ''Synthesis, Characterization and Study of Chromatography Behavior of Novel (Azo–Anil)-Heterocyclic Compounds,'' Asian J. Research Chem, vol. 7(8), pp. 702-710, 2014.
N. I. Taha, ''Synthesis of 1,3-Oxazepine Derivatives Derived from 2-(1H-Benzo[d][1,2,3]Triazol-1-yl) Acetohydrazide by Using Microwave Irradiation,'' International Journal of Organic Chemistry, vol. 7, pp. 219-228, 2017.
N. M. Aljamali, ''Preparation and Identification of Macrocycles of Oxazepine Compounds,'' Journal of Scientific and Innovative Research, vol. 2(1), pp. 53-60, 2013.
N. M. Aljamali, ''Synthesis and Identification of Oxazipen ,Diazipene Compounds Via Peri cyclic Reactions,'' J Chem & Cheml Sci, vol. 3, pp. 64-69, 2013.
P. Verma, S. Gupta, and V. S. Yadav, ''Catalyst-Free and Facile Green Synthesis of Some Novel Oxazepine Derivatives,'' Der Chemica Sinica, vol. 6, pp. 86-89, 2015.
R. Ghosh, SH. Rahaman, C. Lin, TB. Lu, and K. Ghosh, ''Coordination behaviour of symmetrical hexadentate N-donor Schiff bases towards zinc (II) pseudohalides,'' Syntheses, crystal structures and luminescence. Polyhedron, vol. 25, pp. 3104-3112, 2006.
R. M. Al-juburi, ''Synthesis and Characterization of Some Heterocyclic Compounds (Oxazepine, Tetrazole) Derived from Schiff Bases,'' Journal of Al-Nahrain University, vol. 15, pp. 60-67, 2012.
S. J. Wadher, M. P. Puranik, N. A. Karande, and P. G. Yeole, ''Synthesis and Biological Evaluation of Schiff base of Dapsone and their derivative as Antimicrobial agents,'' International Journal of PharmTech Research, vol. 1(1), pp. 22-23, 2009.
S. Mohammed, A. Dawood and M. Mohammed, ‘’Synthesis, Identification and Biological Activity of some Schiff Bases derived from 1,5-diamino naphthalene substrate,’’ Research Journal of Chemistry and Environment, vol. 23(9), pp. 108-122, 2019.
Y. H. Jian, S. Wenhua, Z. L. Li, and Z. Ma, ''The rapid synthesis of Schiff-base without solvent under microwave irradiation,'' Chinese Chemical Letters, vol. 13(1), pp. 3-6, 2002.
Z. H. Abood, ''Using A pericyclic Reactions for The Synthesis of New 1, 3-Oxazepine Compounds From New Imines,'' Journal of Kerbala University, vol. 8(1), pp. 354-370, 2010.
Z. H. Abood, R. T. Haiwal, H. T. ghanin, S. M. Radhi, ''Synthesis of Some New Schiff Bases, Tetrazole and 1,3-Oxazepine Derivatives Containing Azo Group and 1,3,4- Thiadiazole Moiety,'' Journal of Babylon University/Pure and Applied Sciences, vol. 21(1), pp. 181-205, 2013.
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2020-03-30
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Dawood, A. A., Mohammed, S. R., & Mahmoud, M. (2020). Synthesis, Identification and Biological Activity of New Heterocyclic Compounds from Reaction of New Schiff-Bases with Phathalic Anhydride. Science Journal of University of Zakho, 8(1), 12–18. https://doi.org/10.25271/sjuoz.2020.8.1.641
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