Abstract
2-Methylamino-4,4-disubstituted-5-carboethoxymethyl-δ2-1,3,4-oxadiazolin -4-ium chlorides were obtained from the reaction of 1,1-disubstituted-4-methylsemicarbazides with ethyl propiolate in the presence of hydrochloric acid. After hydrolysis of the ester these chlorides recyclize in acetic anhydride to 1-substituted-3-acetoxy-1H-pyrazoles. The difference in the direction of ring opening with acetic anhydride in the betaines of 1,3,4-oxadiazolin-5-acetic acids and their thia-analogs has been demonstrated.
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V. Ya. Kauss, A. F. Mishnev, and I. Ya. Kalvin'sh. Khim. Geterotsikl. Soedin., No.12, 1674 (1992).
V. Ya. Kauss, S. Kh. Grinberga, and I. Ya. Kalvin'sh. Khim. Geterotsikl. Soedin., No. 12, 1680 (1992).
D. H. Kim. J. Heterocycl. Chem., 13, No. 2, 179 (1976).
V. F. Lipnitskii and O. P. Shvaiko. Khim. Geterotsikl. Soedin., No. 12, 1689 (1988).
W. Sucrow, C. Mentzel, and M. Slopianka. Chem. Ber., 111, 780 (1978).
K. A. Jensen, U. Anthoni, B. Kagi, Ch. Larsen, and C. Pedersen. Acta Chem. Scand., 22, No. 1, 1 (1968).
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 12, pp. 1685–1688, 1992.
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Kauss, V.Y., Kalvin'sh, I.Y. 2-Amino-4,4-disubstituted-5-carboxymethyl-Δ2-1,3,4-oxadiazolin-4-ium chlorides and their recyclization in acetic anhydride. Chem Heterocycl Compd 28, 1449–1452 (1992). https://doi.org/10.1007/BF00531302
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DOI: https://doi.org/10.1007/BF00531302