Journal of Global Pharma Technology
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1 Journal of Global Pharma Technology ISS: Available nline at RESEARCH ARTICLE Synthesis, Characterization of Some ew Heterocyclic Derivatives Asstabraq Mohsin Yasir Department of Chemistry, Faculty of Science, AL-Muthanna University, Iraq. Abstract The newly compounds containing a seven-member ring oxazepane and five-member ring tetrazole derivatives were prepared starting schiff bases. Synthesized by percyclic reactions of imine group with phthalic anhydride resulted the formation of 1,3-oxazepane-4,7dione derivatives (S1, ). The new tetrazole derivatives were obtained from treatment of each prepared schiff bases S and S1 with sodium azide to give derivatives (S2, T). Finally derivatives have been characterized by melting points, FT.IR and 1 H-MR spectroscopy. Keywords: Phathalic anhydride, Sodium azide, Tetrazole, xazepane-4,7dione. Introduction Heterocyclic compounds (oxazepine and tetrazole) five-seven membered rings have occupied an important class of organic compounds in medicinal, agricultural and industrial field. 1-3 The structure of oxazepane-4,7diones involves of an unsaturated seven member ring along with two carbonyl group. Tetrazole ring is non-homologous containing four nitrogen atoms and one carbon atom in position. 4 Synthesis of oxazepine and tetrazole ring which is a type from a pericyclic reactions. 5,6 Cycloaddition reaction was classified as a 5+2, implying five-membered component of phthalic anhydrides was added to plus two atoms of imine group leading give a sevenmembered cyclic ring. 7,8 The mechanism of the reaction that used to synthesis of tetrazole ring was classified as 2+3, the common features of this kind of reactions is best accommodated by a transition state geometry between two atoms of the first component of imine group with three atoms of the second component azide group as 1,3-dipolar molecule in Scheme(1). 6 Ar H C C H Ar Scheme 1: Approximate transition state geometry for azide group addition to azomethene of synthesis tetrazole ring Experimental Part Materials and Instruments The chemicals that used in this research were obtained from Fluka, Aldrich and Merck, further purification was not needed. 1 H-MR were recorded on Bruker spectrometer, operating at 400 MHZ were made at the University of Asfahan, Repablic of Islamic Iran. FT-IR spectra were recorded , JGPT. All Rights Reserved 806
2 on FT-IR 8400S, Schimadzu- Spectrophotometer and using KBr discs measurements were made at the college of science, University of AL-Muthanna. Melting points were dependent on SMP30 Stuart melting point apparatus. Preparation Methods Synthesis of, -dibenzylidenebenzene-1,4- diamine (S) 9 A solution of the benzaldehyde (0.02 mol, 2.2 gm) was dissolved in (25ml) of absolute ethanol containing a few drops of glacial acetic acid was added with stirring of 4- Phenylenediamine (0.0l mol, 1.1 gm).the mixture was refluxed with magnetically stirred for 2 hrs. Then, the solvent was removed and cooling, the resulting crystalline and filtered dried and recrystallized from ethanol M.P C, (2.31 gm, 80 % yield). Synthesis of 3-(4--benzlidenebenzeneimine)- 2-phenyl-2,3-dihydrobenzo-1,3-oxazepine-4,7- dione (S1) The oxazepine derivative was synthesize by addition of the phthalic anhydride (0.5 mmol, 0.07gm) to imine compound S (0.5mmol,0.14 gm) with stirring, in dry benzene (15 ml) was added and refluxed until the precipitate formed 6 hrs. The solvent was removed and the resulting precipitates dried out and recrystallized from ethanol. M.P C, (0.18 gm, 86 % yield). Synthesis of 3-(5-phenyl-4,5-dihydro -1H- tetrazole-1-yl)-2-phenyl-2,3-dihydrobenzo-1,3- oxazepine-4,7-dione (S2) To a stirred solution of oxazepine derivative S1 (0.6mmol, 0.26 gm) was dissolved in (10mL) of dry benzene was added to solution of sodium azide (0.6mmol, 0.04 gm) in (10mL) of dry benzene. The reaction mixture was refluxed with stirring for 8 hrs. Then, the solvent was removed and the resulting precipitate was shaped collected by filtration, dried up and recrystallized from ethanol. M.P C, (0.21 gm, 72 % yield). Synthesis of 1,4-Bis(2-phenyl-2,3- dihydrobenzo-1,3-oxazepine-4,7-dione) benzene () The compound was prepared by the reaction of Schiff bases S (0.6 mmol, 0.17 gm) transferred to the round bottom flask containing in (25 ml) of dry benzene and added phthalic anhydride (0.6 mmol, 0.09 gm). The reaction mixture was refluxed with stirring for 8 hrs. The producing precipitate was recrystallized from ethanol. M.P C, (0.31 gm, 89 % yield). Synthesis of 1, 1 -benzene-1,4-diylbis(5- phenyl-4,5-dihydro-1h-tetrazole)(t) A mixture of imine derivative (0.5 mmol, 0.14gm) was dissolved in (15mL) of dry benzene was added to solution of sodium azide (0.5 mmol, 0.03gm) in (10mL) of dry benzene. The mixture was refluxed for 7 hrs. The precipitate was cooled and filtered, dried up and recrystallized from ethanol. M.P C, (0.15 gm, 83 % yield). Results and Discussion The new synthesized derivatives were characterized by its FT.IR spectra, and 1 H- MR. The FT.IR spectrum ν cm -1, Fig.1 of the schiff base (S) showed appearance of the stretching vibration at 1616 (C=) exocyclic azomethine group, 3057 (C-H Aromatic), and disappearance of the stretching vibration of H2 group. Fig. 2 of the derivative S1 showed 1708 (C= of lactone group), 1683 (C= of lactam group). Fig. 3 showed appearance of the stretching vibration at 3317 (-H), 3055 (C-H of Aromatic), 1616 (C=) inside tetrazole ring, and 2123 (-3 of azide group). 5 Fig. 4 of the derivative () showed 1693 (C= lactone), 1587 (C= lactam), 3082 (C-H Aromatic). Finally, Fig.5 of the tetrazole (T) showed 3390 (-H) tetrazole ring, (azide group). The 1 H-MR (DMS-d6) δ (ppm): as shown in Fig.6 of the Schiff base S: 8.57 (s, 2H; HC=) imine proton, (d, 4 H; Ar- H), (s, 10 H; Ar-H). Fig. 7 of the derivative S1: 7.99 (s, 1H; HC=), aromatic protons, (s, 1H; C-H) oxazepine ring. 1 H-MR spectrum, Fig. 8 of the derivative showed the doublet signal at (Ar-H), 8.25(s, 2H; C-H) oxazepine ring. The structure of all derivatives is presented in Scheme , JGPT. All Rights Reserved 807
3 2 H EtH (abs) H + / 65 C o Dry Benzene/50 C o H 2 (S) (S 1 ) Dry Benzene/50 C o 2a 3 Dry Benzene/50-60 C o a 3 Dry Benzene/50-60 C o () (T) (S 2 ) Scheme 2: Synthesis of heterocyclic derivatives from schiff base Fig. 1: FT.IR Spectrum for Schiff base S Fig. 2: FT.IR Spectrum for derivative S1 Fig. 3: FT.IR Spectrum for derivative S , JGPT. All Rights Reserved 808
4 Fig. 4: FT.IR Spectrum for derivative Fig. 5: FT.IR Spectrum for derivative T Fig. 6: 1 H-MR Spectrum for Schiff base S Fig. 7: 1 H-MR Spectrum for derivative S , JGPT. All Rights Reserved 809
5 Conclusion Conducting a research of preparation of new 1, 3-oxazepine-4,7dione and tetrazole derivatives from reaction imine was reacted with phthalic anhydride to give 1, 3- oxazepine-4,7dione derivatives were also Fig. 8: 1 H-MR Spectrum for derivative reacted with sodium azide to give tetrazole derivatives. The compounds were characterization by its 1 H-MR and FT.IR spectrum confirm this preparation. References 1. T Eicher, S Hauptmann (2003) Wiley-VCH, 2 nd ed BS Holla, PM Akberali, MK Shivananda (2001) 56, BS Holla, K Poorjary, SB Rao, MK Shivananda (2002) Eur. J. Med. Chem, 37, CL Allaway, M Daly, M ieuwenhuyzen, GC Saunders (2002) J. Fluo. Chem, 115, ZH Abood (2010) J Kerbala University, 8, IY Majeed, D AL-Saady, SA Saoud (2013) J. for Sci. and Technol, 3, ZH Abood, RT Haiwal, IL Kadum (2008) J. Kerbala University, 6, F Al-mran, RM Mohareb, A El-Khair (2002) J. Hetero. Chem, 39, HA Abdel Moniem, RM Abdel Maaboud, et.al (2013) J. of Cosm. Derm. Sci. & Appl, KJ Kadhim, MG Munahi (2017) J. of Global Pharma Technol, 9, F Al-Hite, H Abid, A Al-Hadithi (2007) J. Sci. Um-Salama. 2, , JGPT. All Rights Reserved 810
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