SYNTHESIS, CHARACTERIZATION AND KINETIC STUDIES OF SOME OXAZEPINE AND OXAZEPANE DERIVATIVES | ||
| Journal of University of Anbar for Pure Science | ||
| Article 7, Volume 1, Issue 3, December 2007, Pages 22-40 PDF (661.31 K) | ||
| Document Type: Research Paper | ||
| DOI: 10.37652/juaps.2007.15601 | ||
| Authors | ||
| Waleed F. AL-Hity1; Khalid F.Al-Rawi2; Mohammed A.Al-Hadithi* 2 | ||
| 1Chemistry Department - College of Education for woman - Anbar University | ||
| 2Department of Chemistry - College of Science - University of Anbar | ||
| Abstract | ||
| 1,3-Bis(2-hydroxy-benzylidene)-Thiourea and 1,3-Bis-(dimethylamino-benzylidene)-Thiourea were prepared by condensation of Thiourea with one equivalent and two equivalent of substituted benzaldehyde. These Schiff-bases were reacted with one equivalent of Maleic , Succinic and Phthalic anhydride in absolute ethanol to give 7-membered heterocyclic ring system of 2-(2-Hydroxy-phenyl)-4,7-dioxo-4,7-dihydro-[1,3] oxazpine-3-carbothioic acid amide and 2-(4-Dimethylamino-phenyl)-4,7-dioxo-4,7-dihydro-[1,3]oxazepine-3-carbothioiacid amide , 1,3-Bis(2-hydroxy-benzylidene)-Thiourea and 1,3-Bis-(dimethylamino-benzylidene)-Thiourea were reacted with two equivalent of Maleic and Succinic anhydride in same solvent to give 2 (7-membered) heterocyclic ring system of 2-(2-hydroxy-phenyl)-3-[2-(2-hydroxy-phenyl)-4,7-dioxo-[1,3]oxazepine-3-carbothioyl]-2,3-dihydro-[1,3]oxazepine-a,7-dione and 2-(4-Dimethylamino-phenyl)-3-[2-(4-dimethylamino-phenyl)-4,7-dioxo-[1,3]oxazepine-3- carbothioyl]-2,3-dihydro-[1,3]oxazepine-4,7-dione. The constants of reaction velocity for (Schiff-bases)with Maleic , Succinic and Phthalic anhydride were studied and showed that the reaction wsa first – order one .Some of thermodynamic characteristics were evaluated and showed differences among the prepared compounds . The final products were identified by their melting points, elemental analysis, IR, 1H NMR and UV-Visible spectra. | ||
| Keywords | ||
| Schiff bases; Oxazepan; oxazepine; synthesis; properties; kinetic studies | ||
| References | ||
|
[1]-Toshio, M., Tsutomu, K., and Osamu, S., (photochemical and thermal reactions of some heterocyclic containing C=N-O and N=C-O group) Pure and Appl. Chem.Vol.49, pp. 287-308, 1977.
[2]- Cheesman,G. and Greenberg ,S. (Synthesis of 5,6-dihydro- 4H-pyrrolo[1,2-α] [1,4] benzodiazepines) J.Heterocyclic Chem. 16,241, 1979.
[3]- Schiff, H. Ann, 131,118, 1864.
[4]- Clifford J. Crewell, Olaf, A. Rungvist, and Malcolm M. Campbell, (spectral analysis of organic compounds), 2nd ed., Longman, 1972.
[5]-Takashi, T., Takeo, T., and Yashizo, S., (Synthesis andcycloaddition reaction of di and tri- substituted 1,3- oxazepine ) Heterocycles, 11, 331-6. 1978.
[6]-Tyoji, T., Kuniyoshi, I., and Takashi, T., Chem. Pharm. Bull., 35 (8), 74, 1987.
[7]- Biginelli, P.,Gazz., Chim. Ital., 23, 360, 1983.
[8]-Lin, H.., Zhang, X.; Cheng, L..Chin., Chem. Lett., 10 (11), 915-916, 1999.
[9]- Fahad,A., Hussein, Obad,H., Abid, (synthesis of N- substituted saccharin's via Schiff Bases)., Iraqi Journal of Chemistry, Vol 26,No.(1),pp.42-50, 2000 .
[10]- Fahad,A., Hussein, Obad,H., Abid, (synthesis of N- substituted saccharin's via Schiff Bases) . Iraqi Journal of Chemistry, Vol 26, No. (1) pp.35-41, 2000.
[11]- Fahad, A., Hussein, et al. (Synthesis of some Barbiturates via Schiff bases).Iraqi Journal of Chemistry, Vol 26, No.(1) pp.216-274, 2000.
[12]- Huisgen, R., Angew, Chem. Internt., Edit. 7,321, 1968.
[13]- Robert, M.Moriarty and charless w.Jefford (Organic chemistry A problms: An Approach,) W.A. Bengamine, Inc,p 526 , 1975.
[14]- Al-Hadithi, Mohammed, (Synthesis, characterization and kinetic studies of ethylene-[1,3]oxazinan......) Univ of Sharjah journal of pure & applied science ,Vol. 3 , No .3 pp -25-24, 2006 .
[15]- Al-Hity, waleed, Alhadithi, Mohammed (Synthesis, Characterization and Kinetic Studies of Oxazepine and Oxazepane from reaction of 1,3-Bis(2-hydroxy-benzylidene)- urea.....) Journal of Al- Nahrain Univ, Vol. 8 (2) pp- 32-39, 2005 | ||
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