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

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Chemistry of Heterocyclic Compounds Aims and scope

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.

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Authors
  1. V. A. Mamedov
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  2. L. V. Krokhina
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  3. E. A. Berdnikov
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  4. Ya. A. Levin
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Additional information

A. E. Arbuzov Institute of Organic and Physical Chemistry, Kazan Science Center, Russian Academy of Sciences, Kazan 420083. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 9, pp. 1266–1272, September, 1996. Original article submitted June 19, 1996.

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Mamedov, V.A., Krokhina, L.V., Berdnikov, E.A. et al. Synthesis and reactions of 2-amino-5-carbomethoxy-6-phenyl-6H-1,3,4-thiadiazine. Chem Heterocycl Compd 32, 1089–1094 (1996). https://doi.org/10.1007/BF01164718

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