Interaction of 5-chloro-1-phenyl-1H-pyrazole-4-carboxamide and 5-chloro-N-formyl-1-phenyl-1H-pyrazole-4-carboxamide with hydrazine hydrate

Authors

  • A. O. Gurenko Institute of Bioorganic Chemistry and Petrochemistry of the NAS of Ukraine, Ukraine
  • B. M. Khytova Institute of Bioorganic Chemistry and Petrochemistry of the NAS of Ukraine, Ukraine
  • S. V. Klyuchko Institute of Bioorganic Chemistry and Petrochemistry of the NAS of Ukraine, Ukraine
  • O. M. Vasilenko Institute of Bioorganic Chemistry and Petrochemistry of the NAS of Ukraine, Ukraine
  • V. S. Brovarets Institute of Bioorganic Chemistry and Petrochemistry of the NAS of Ukraine, Ukraine

DOI:

https://doi.org/10.24959/ophcj.14.759

Keywords:

pyrazole, pyrazole-4-carboxamide, pyrazole-4-carbohydrazide, hydrazine hydrate

Abstract

This article represents the research of the interaction of 1-phenyl-5-chloro-1H-pyrazole-4-carboxamide and 1-phenyl-N-formyl-5-chloro-1H-pyrazole-4-carboxamide with hydrazine hydrate in order to get pyrazole derivatives as potential bioactive substances. It has been found that during the short (~40 min) boiling of 1-phenyl-5-chloro-1H-pyrazole-4-carboxamide with hydrazine hydrate a previously unknown 5-hydrazino-1-phenyl-1Hpyrazole-4-carbohydrazide with the yield of 50% is formed. The further boiling (~15 h) of the product obtained with hydrazine hydrate leads unexpectedly to 1-phenyl-1H-pyrazole-4-carbohydrazide. The probable mechanism of its obtaining, which includes dimerization of the prototropic isomer formed while cleaving the hydrazine molecule and the further elimination of the nitrogen molecule, has been considered. When boiling with hydrazine hydrate for 3 hours 1-Phenyl-N-formyl-5-chloro-1H-pyrazole-4-carboxamide gives 5-amino-1-phenyl-1H-pyrazole-4-carbohydrazide. At first, obviously, N-[(5-hydrazino-1-phenyl-1H-pyrazol-4-yl) carbonyl]formamide is formed with further cyclization into pyrazole[3,4-d][1,2,3]triazin-4-one. The latter eliminates the nitrogen molecule when heating with the formation of the reactive 4-carbonyl-1-phenyl-4,5-dihydro-1H-pyrazole-5-imine. Addition of hydrazine to it leads to 5-amino-1-phenyl-1H-pyrazole-4-carbohydrazide. The composition of all compounds synthesized has been proven by elemental analysis and the structure has been confirmed by spectroscopic methods.

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Published

2014-03-06

How to Cite

(1)
Gurenko, A. O.; Khytova, B. M.; Klyuchko, S. V.; Vasilenko, O. M.; Brovarets, V. S. Interaction of 5-Chloro-1-Phenyl-1H-Pyrazole-4-Carboxamide and 5-Chloro-N-Formyl-1-Phenyl-1H-Pyrazole-4-Carboxamide With Hydrazine Hydrate. J. Org. Pharm. Chem. 2014, 12, 56-59.

Issue

Vol. 12 No. 1(45) (2014)

Section

Original Researches

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