Chemistry of Heterocyclic Compounds

, Volume 28, Issue 12, pp 1449–1452 | Cite as

2-Amino-4,4-disubstituted-5-carboxymethyl-Δ2-1,3,4-oxadiazolin-4-ium chlorides and their recyclization in acetic anhydride

  • V. Ya. Kauss
  • I. Ya. Kalvin'sh


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.


Acetic Chloride Ester Hydrolysis Ethyl 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.


Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.


  1. 1.
    V. Ya. Kauss, A. F. Mishnev, and I. Ya. Kalvin'sh. Khim. Geterotsikl. Soedin., No.12, 1674 (1992).Google Scholar
  2. 2.
    V. Ya. Kauss, S. Kh. Grinberga, and I. Ya. Kalvin'sh. Khim. Geterotsikl. Soedin., No. 12, 1680 (1992).Google Scholar
  3. 3.
    D. H. Kim. J. Heterocycl. Chem., 13, No. 2, 179 (1976).Google Scholar
  4. 4.
    V. F. Lipnitskii and O. P. Shvaiko. Khim. Geterotsikl. Soedin., No. 12, 1689 (1988).Google Scholar
  5. 5.
    W. Sucrow, C. Mentzel, and M. Slopianka. Chem. Ber., 111, 780 (1978).Google Scholar
  6. 6.
    K. A. Jensen, U. Anthoni, B. Kagi, Ch. Larsen, and C. Pedersen. Acta Chem. Scand., 22, No. 1, 1 (1968).Google Scholar

Copyright information

© Plenum Publishing Corporation 1993

Authors and Affiliations

  • V. Ya. Kauss
    • 1
  • I. Ya. Kalvin'sh
    • 1
  1. 1.Latvian Institute of Organic ChemistryRigaLatvia

Personalised recommendations