Abstract
2-[β-(Phenylamino)vinyl]-5-(1,1-dimethyl-2-acetoxyethyl)-4(5H)-oxazolonium perchlorate was synthesized. The deprotonation ability of this compound in chloroform by the action of sodium carbonate to give 4(5H)-oxazolone, containing enamine fragment at C(2) in the ring was studied. Z,E-Isomerization at the double bond was found at room temperature by the action of the solvents.
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REFERENCES
T. P. Kosulina, N. V. Bychenko, I. P. Morenets, L. N. Sorotskaya, E. Krutoshikova, N. I. Valter, and V. G. Kulnevich, Khim. Geterotsikl. Soedin., 986 (1998).
T. P. Kosulina, I. N. Kozlovskaya, N. V. Bychenko, I. P. Morenets, and V. G. Kulnevich, Khim. Geterotsikl. Soedin., 2336 (1995).
H. Kessler, G. Zimmermann, and H. Förster, Angew. Chem., 93, 1085 (1981).
V. G. Kulnevich, T. P. Kosulina, F.-U. Lyubke, and Z. I. Zelikman, Khim. Geterotsikl. Soedin., 30 (1980).
J. Emsly, J. Finney, and L. Sutcliffe, High-Resolution NMR Spectroscopy, Vol. 2, Mir, Moscow (1969).
V. I. Bakhmutov, K. A. Kochetkov, and E. I. Fedin, Izv. Akad. Nauk SSSR, Ser. Khim., 1295 (1980).
V. G. Granik, A. M. Zhidkova, N. S. Zhivotavskaya, N. P. Solov'eva, and M. K. Polievktov, Zh. Org. Khim., 17, 2421 (1981).
V. M. Potapov, Stereochemistry[in Russian], Khimiya, Moscow (1988).
B. A. Shainyan and A. N. Mirskova, Usp. Khim., 48, 201 (1979).
F.-U. Lubcke, T. P. Kosulina, and V. G. Kulnevich, Khim. Geterotsikl. Soedin., 894 (1981).
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Kosulina, T.P., Pushkareva, K.S., Morenets, I.P. et al. Substituted 4(5H)-Oxazolones and Their Salts. 10. Synthesis of 2-[β-(Phenylamino)vinyl]-4(5H)-oxazolones from Their Salts and Z,E-Isomerization at the Double Bond. Chemistry of Heterocyclic Compounds 37, 484–489 (2001). https://doi.org/10.1023/A:1017608122606
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DOI: https://doi.org/10.1023/A:1017608122606