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

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Chemistry of Heterocyclic Compounds Aims and scope

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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Authors and Affiliations

  1. Latvian Institute of Organic Chemistry, LV-1006, Riga, Latvia

    V. Ya. Kauss & I. Ya. Kalvin'sh

Authors
  1. V. Ya. Kauss
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  2. I. Ya. Kalvin'sh
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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

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