EFFICIENT ONE-POT SYNTHESIS OF 3-(POLYFLUOROALKYL)PYRAZOL-4-AMINES

Authors

  • Vera I. Filyakova Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences, 20 S. Kovalevskoi St., Yekaterinburg 620108, Russia
  • Nadezhda S. Boltacheva Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences, 20 S. Kovalevskoi St., Yekaterinburg 620108, Russia
  • Pavel A. Slepukhin Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences, 20 S. Kovalevskoi St., Yekaterinburg 620108, Russia Institute of Chemical Engineering, Ural Federal University, 28 Mira St., Yekaterinburg 620002, Russia
  • Valery N. Charushin Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences, 20 S. Kovalevskoi St., Yekaterinburg 620108, Russia Institute of Chemical Engineering, Ural Federal University, 28 Mira St., Yekaterinburg 620002, Russia

DOI:

https://doi.org/10.1007/7265

Keywords:

5-alkyl/hetaryl-4-amino-3-(polyfluoroalkyl)pyrazoles (4-aminopyrazoles), organofluorine compounds, 3-polyfluoroalkyl-1, 3-diketonates, 3-(polyfluoroalkyl)pyrazol-4-amines, green chemistry, one-pot synthesis, X-ray analysis.

Abstract

A simple convenient one-pot protocol for the synthesis of 5-alkyl/hetaryl-4-amino-3-(polyfluoroalkyl)pyrazoles (4-aminopyrazoles) has been suggested. The method is based on using readily available lithium 3-polyfluoroalkyl-1,3-diketonates and sodium nitrite as starting materials and hydrazine hydrate for cyclization into 4-nitroso-3-(polyfluoroalkyl)pyrazoles, followed by reduction of the latter into target products. Molecular structures of 5-methyl-, 5-(thiophen-2-yl)-, 5-(4-methylphenyl)-, and 5-(pyridin-2-yl)-substituted 3-trifluoromethyl-1H-pyrazol-4-amines have been established by X-ray analysis.

Author Biographies

Vera I. Filyakova, Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences, 20 S. Kovalevskoi St., Yekaterinburg 620108, Russia

Доктор химических наук, профессор, ведущий научный сотрудник

Nadezhda S. Boltacheva, Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences, 20 S. Kovalevskoi St., Yekaterinburg 620108, Russia

кандидат химических наук, научный сотрудник ИОС им. И.И. Постовского Уральского отделения Российской академии наук.

Pavel A. Slepukhin, Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences, 20 S. Kovalevskoi St., Yekaterinburg 620108, Russia Institute of Chemical Engineering, Ural Federal University, 28 Mira St., Yekaterinburg 620002, Russia

кандидат химических наук, старший научный сотрудник ИОС им. И.И. Постовского Уральского отделения Российской академии наук.

Valery N. Charushin, Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences, 20 S. Kovalevskoi St., Yekaterinburg 620108, Russia Institute of Chemical Engineering, Ural Federal University, 28 Mira St., Yekaterinburg 620002, Russia

Руководитель отдела стратегии и развития,профессор, действительный член Российской академии наук

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Published

2023-09-04

Issue

Vol. 59 No. 8 (2023)

Section

Original Papers