Synthesis and reactions of 2-amino-5-carbomethoxy-6-phenyl-6H-1,3,4-thiadiazine

Authors

  • B. А. Мaмедов A. E. Arbuzov Institute of Organic and Physical Chemistry, Kazan Science Center, Russian Academy of Sciences, Kazan 420083
  • Л. В. Крохина A. E. Arbuzov Institute of Organic and Physical Chemistry, Kazan Science Center, Russian Academy of Sciences, Kazan 420083
  • E. А. Бердников A. E. Arbuzov Institute of Organic and Physical Chemistry, Kazan Science Center, Russian Academy of Sciences, Kazan 420083
  • Я. А. Левин A. E. Arbuzov Institute of Organic and Physical Chemistry, Kazan Science Center, Russian Academy of Sciences, Kazan 420083

Abstract

Treatment of methyl 3-phenyl-3-chloro-2-oxopropionate with thiosemicarbazide gives 2-amino-S-carbomethozy6-phenyl-6H-1,3,4-thiadiazine, theisomeric 2-hydrazino-4-carbomethoxy-S-phenylthiazole, orthecorresponding carboxylic acids depending on the acidity of the medium. The intermediate on the way to the thiadiazine proved to be a covalent 4,5-hydrate. These reactions are subject to thermodynamic control. Acetylation of the above thiadiazine occurs either with retention of the thiadiazine structure or via sulfur atom extrusion to give acetylated 3-amino-4-phenyl-5-carbomethoxypyrazole.

How to Cite
Mamedov, V. A.; Krokhina, L. V.; Berdnikov, E. A.; Levin, Ya. A. Chem. Heterocycl. Compd. 1996, 32, 1089. [Khim. Geterotsikl. Soedin. 1996, 1266.]

For this article in the English edition, see DOI https://doi.org/10.1007/BF01164718

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Published

1996-09-25

Issue

No. 9 (1996)

Section

Original Papers