New reaction products of acetylacetone with semicarbazide derivatives

Vera S. Glukhacheva, Sergey G. Il'Yasov, Igor V. Kazantsev, Elena O. Shestakova, Dmitri S. Il'Yasov, Ilia V. Eltsov, Andrey A. Nefedov, Yuri V. Gatilov

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Abstract

A new approach is suggested herein for the synthesis of pyrazole derivatives by reacting 4-nitrosemicarbazide with acetylacetone. Additional studies were done on the reaction of acetylacetone with semicarbazide and its derivatives (4-aminosemicarbazide, methylsemicarbazide, and dimethylsemicarbazide). The study on the reaction with acetylacetone resulted in monocyclic 3, 5-dimethyl-N-nitropyrazole-1-carboxamide, monocyclic 5-hydroxy-3, 5-dimethyl-2-pyrazoline, and bicyclic bis(3, 5- dimethylpyrazole-1-carbonyl)hydrazine, and conditions for the formation of acetone semicarbazone were identified. The structures of the resultant compounds were validated by physicochemical analytical methods, including X-ray diffraction. The computer-aided screening in the PASS prediction software discovered a high biological activity of the newly obtained compounds.

Original languageEnglish
Pages (from-to)8637–8645
Number of pages9
JournalACS Omega
Volume6
Issue number12
DOIs
Publication statusPublished - 30 Mar 2021

OECD FOS+WOS

  • 2.04 CHEMICAL ENGINEERING
  • 1.04 CHEMICAL SCIENCES

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