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New Reaction Products of Acetylacetone with Semicarbazide Derivatives.

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.

SUBMITTER: Glukhacheva VS

PROVIDER: S-EPMC8015095 | biostudies-literature | 2021 Mar

REPOSITORIES: biostudies-literature

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New Reaction Products of Acetylacetone with Semicarbazide Derivatives.

Glukhacheva Vera S VS Il'yasov Sergey G SG Kazantsev Igor V IV Shestakova Elena O EO Il'yasov Dmitri S DS Eltsov Ilia V IV Nefedov Andrey A AA Gatilov Yuri V YV

ACS omega 20210317 12

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-<i>N</i>-nitropyrazole-1-carboxamide, monocyclic 5-hydroxy-3,5-dimethyl-2-pyrazoline, and bicyclic <i>bis</i>(3,5-di ...[more]

PMID: 33817525

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