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.

Two-Component versus Three-Component Condensations in the Race between Hydrazide, Triketone, and Hydrogen Peroxide-How do All Six Reactive Centers Cooperate to Incorporate the Most Diverse Set of Heteroatomic Bridges in a Tricyclic Frame?

“…Surprisingly, the peroxide byproduct 4a was formed only in minor amounts, even under the excess of H 2 O 2 . The expected – hydrazones, pyrazole, and dihydropyridine derivatives were not observed. Remarkably, products which retained an unreacted carbonyl group were not observed.…”

“…Remarkably, a mixture of antagonistic reactants, including highly oxidizing H 2 O 2 , could be directed down a constructive path. Counterintuitively, the complex three-component condensation turned out to be preferred over the well-known formation of hydrazones or derivatives of pyrazoles and dihydropyridines. – …”

Synthesis and Characterization of Some New Pyrazole, Triazole, Oxadiazole, Thiazole, Thiadiazole Derivatives Bearing p-Toluenesulfonamide

“…Then the mixture was cooled to form a precipitate which was filtered, washed with water and dried. 30 White solid, ( 0.23 g, 79%), m.p= 205-207 °C. FT-IR ν (cm -1 ): 1159, 1338 (SO2), 1606 (C=N), 1693 (C=O), 2985 (CH), 3062 (=CH), 3219 (NH).…”

Synthesis of Mono and Bis-Substituted Compounds 1-(2-hydroxybenzylidene) Carbonohydrazide and 1, 5-bis(2-Hydroxybenzaldehyde) Carbohydrazone: Study Spectroscopy and X-ray Diffraction

“…"Many of these carbohydrazide derivatives are used as precursors in the preparation of heterocyclic compounds with interesting biological properties" [7]. Some of them have made it possible to develop drugs with a broad spectrum of activity such as antimicrobial [8], anticonvulsant [9], antidepressant [10], antioxidant [11], analgesic [12], antifungal [13], antiplatelet [14], antituberculosis [15], anti-HIV [16], inflammatory [17], antidiabetic [18], anticancer [19], and antimalarial [20]. "Due to the presence of several donor atoms in these derivatives and the possibility for these molecules to appear in different conformations, they can be used in coordination chemistry.…”