Azoles and azines. 62. Structure of 2-aryl-1,3-oxazine-4,6-diones
- 40 Downloads
1H,13C NMR, IR, and UV spectra have been studied for solutions of a number of potentially tautomeric 2-aryl-1,3-oxazine-4,6-diones and their 5-methyl substituted analogs with variation of substituent at the para position of the benzene ring, as well as compounds with a fixed structure that simulates possible tautomeric forms. The data have been compared with the results of quantum chemical calculations carried out in SSO MO LCAO approximation by the CNO, CNDO/2, and MPNDO/3 methods. In DMSO and THF solution the test compounds exist predominantly as 2-aryl-4-hydroxy-6H-1,3-oxazin-6-ones. The para substituent in the benzene ring does not affect the composition of the tautomer mixture significantly.
KeywordsBenzene DMSO Diones Benzene Ring Quantum Chemical
Unable to display preview. Download preview PDF.
- 1.V. é. Zakhs, I. P. Yakovlev, B. A. Ivin, Khim. Geterotsikl. Soedin., No. 3, 382 (1987).Google Scholar
- 2.E. Ziegler and H. Meindl, Monatsh. Chem.,95, 1318 (1964).Google Scholar
- 3.J. C. Martin, R. D. Burpitt, P. G. Gott, M. Harris, and R. H. Meen, J. Org. Chem.,36, 2205 (1971).Google Scholar
- 4.Th. Kappe, W. Golser, M. Hariri, and W. Stadlbauer, Chem. Ber.,112, 1586 (1979).Google Scholar
- 5.H. L. Ammon, A. J. Gordon, and R. L. Ehrenkaufer, Acta Crystallogr.,B29, 2619 (1973).Google Scholar
- 6.B. Ya. Simkin and V. I. Minkin, Khim. Geterotsikl. Soedin., No. 2, 177 (1980).Google Scholar
- 7.W. Friedrichsen, E. Kujath, C. Lieberzeit, R. Schmidt, and A. Schwarz, Ann. Chem., No. 10, 1655 (1978).Google Scholar
- 8.J. L. Chitwood, P. G. Gott, and J. Cm. Martin, J. Org. Chem.,36, 2228 (1971).Google Scholar
- 9.G. A. Shembelov, Yu. A. Ustynyuk, V. M. Mamaev, S. Ya. Ishchenko, I. P. Gloriozov, V. B. Luzhkov, V. V. Orlov, V. Ya. Simkin, V. I. Pupyshev, and V. N. Burmistrov, in: Quantum Chemical Methods of Calculating Molecules [in Russian], Yu. A. Ustynyuk (ed.), Khimiya, Moscow (1980), p. 142.Google Scholar
- 10.A. J. Speziale and L. R. Smith, J. Org. Chem.,27, 3742 (1962).Google Scholar
- 11.J. F. Arens, Recl. Trav. Chim.,74, 271 (1955).Google Scholar