CONDITIONS FOR THE SELECTIVE CONVERSION OF QUATERNARY 3-ANILINO-1,5-DIMETHYLPYRAZOLIUM SALTS INTO 3-ANILINO-1,5-DIMETHYLPYRAZOLE

Authors

  • И. Б. Дзвинчук Institute of Organic Chemistry, National Academy of Sciences of Ukraine, Kiev 02094
  • С. А. Карташов Institute of Organic Chemistry, National Academy of Sciences of Ukraine, Kiev 02094
  • А. В. Выпирайленко Institute of Organic Chemistry, National Academy of Sciences of Ukraine, Kiev 02094
  • U. Doller Aventis CropScience Gmbh, D-65926, Frankfurt-on-Main
  • М. О. Лозинский Institute of Organic Chemistry, National Academy of Sciences of Ukraine, Kiev 02094

Keywords:

hydrazines, pyrazoles, dehaloalkylation, quaternization, selectivity, C-sulfonation, cyanoethylation

Abstract

The possibility has been studied of converting quaternary 3-anilino-1,5-dimethylpyrazolium salts into 3-anilino-1,5-dimethylpyrazole, the first representative of the 1-alkyl-3-arylaminopyrazoles. The dependence of the reaction direction on the nature of the substituent at position 2 has been clarified. The most effective result was obtained with a cyanoethyl substituent. On boiling the initial salt with aqueous ammonia the target product is isolated in quantitative yield. Syntheses of the initial salts are described. C-Sulfonation was detected on interacting 3-anilino-1-benzoyl-3-methylpyrazole and dimethyl sulfate, with the formation of p-(3-amino-1,2,5-trimethylpyrazolio)benzenesulfonate.

How to Cite
Dzvinchuk, I. B.; Kartashov, S. A.; Vypirailenko, A. V.; Doller, U.; Lozinskii, M. O. Chem. Heterocycl. Compd. 2004, 40, 570. [Khim. Geterotsikl. Soedin. 2004, 679.]

For this article in the English edition, see DOI 10.1023/B:COHC.0000037311.01960.3e

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Published

2004-05-25

Issue

No. 5 (2004)

Section

Original Papers