SYNTHESIS AND TRANSFORMATIONS OF 3(5)-(3-METHYLFURAZAN-4-YL)-4-NITRO-1<i>Н</i>-PYRAZOLE-5(3)-CARBOXYLIC ACID

Authors

  • Александр В. Корманов N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Ave., Moscow 1
  • Дмитрий Л. Липилин N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Ave., Moscow 1
  • Татьяна К. Шкинева N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Ave., Moscow 1
  • Ирина А. Вацадзе N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Ave., Moscow 1
  • Андрей М. Козеев N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Ave., Moscow 1
  • Игорь Л. Далингер N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Ave., Moscow 1

DOI:

https://doi.org/10.1007/3795

Keywords:

furazan, nitramine, nitropyrazole, nitropyrazolecarboxylic acids, Hofmann rearrangement, nitration

Abstract

Methyl 3-(4-methylfurazan-3-yl)-1Н-pyrazole-5-carboxylate was obtained by condensation of 3-acetyl-4-methylfurazan with diethyl oxalate with subsequent treatment of the β-diketoester intermediate with hydrazine, and was nitrated to produce 3(5)-(3-methylfurazan-4-yl)-4-nitro-1Н-pyrazole-5(3)-carboxylic acid. The amide of this acid was used in a Hofmann rearrangement, providing 3-amino-5-(4-methylfurazan-3-yl)-4-nitro-1Н-pyrazole, nitration of which yielded the respective nitramine.

Authors: Alexandr V. Kormanov, Dmitry L. Lipilin, Tatyana K. Shkineva,
Irina A. Vatsadze, Andrei M. Kozeev, Igor L. Dalinger*

Author Biographies

Александр В. Корманов, N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Ave., Moscow 1

ведущий инженер

Дмитрий Л. Липилин, N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Ave., Moscow 1

н.с., к.х.н.

Татьяна К. Шкинева, N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Ave., Moscow 1

н.с., к.х.н.

Ирина А. Вацадзе, N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Ave., Moscow 1

м.н.с.

Андрей М. Козеев, N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Ave., Moscow 1

инженер-исследователь

Игорь Л. Далингер, N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Ave., Moscow 1

главный научный сотрудник, д.х.н.

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Published

2017-10-03

Issue

Vol. 53 No. 8 (2017)

Section

Original Papers