Chemistry of iminofurans: VI.* Synthesis and structure of 2-(2-ylidenehydrazino)-substituted 4-aryl-4-oxobut-2-enoic and 5,5-dimethyl-4-oxohex-2-enoic acids

The synthesis of new substituted 2-[2-(diphenylmethylene)hydrazinyl]-5,5-dimethyl-4-oxohex-2-enoates is described. The synthesis from commercially available starting materials included the preparation of 5,5-dimethyl-2,4-dioxohexanoic acid via Claisen condensation of 3,3-dimethylbutan-2-one (pinacolone) and diethyl oxalate in the presence of sodium methanolate. The resulting acid reacted with (diphenylmethylene)hydrazine to form 2-[(diphenylmethylene)hydrazono]-5,5-dimethyl-4-oxohexanoic acid. The initial 5-(tert-butyl)-3-[(diphenylmethylene)hydrazono]furan-2(3H)-one was obtained by a known literary method: intramolecular cyclisation of 2-[(diphenylmethylene)hydrazono]-5,5-dimethyl-4-oxohexanoic acid under the action of propionic anhydride. 5-(tert-Butyl)-3-[(diphenylmethylene)hydrazono]furan-2(3H)-one entered the decyclization reaction under the action of primary aromatic alcohols to form substituted 2-[2-(diphenylmethylene)hydrazinyl]-5,5-dimethyl-4-oxohex-2-enoates. The presence of equimolar quantities of triethylamine was important; otherwise, the reaction proceeded with low yields. The isolation of target compounds was carried out by fi ltration of the resulting sediment followed by recrystallization. The structure of the compounds obtained was confi rmed by the 1 H and 13 C NMR spectroscopy methods. The resulting substituted esters exist in a solution of deuterated chloroform in one tautomeric form, in contrast to the previously studied solutions of deuterated DMSO, where up to four tautomeric forms were observed. Analgesic and anti-infl ammatory activity of new and previously synthesized compounds of this series has been studied. Analgesic activity was evaluated by the "Hot Plate" test on outbred white mice of both sexes with intraperitoneal injection. Anti-infl ammatory activity was studied on a carrageenan-induced paw edema model with oral administration of the studied substances. One compound possesses both high analgesic and high anti-infl ammatory effects, which causes the prospects for its use as a pharmacologically active substance.

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“…Initial compounds 3, 4, 1b were synthesized according to the known procedures described in [49,50]; all parameters correspond to literature data.…”

Section: Methodsmentioning

confidence: 99%

Synthesis and Biological Activity of Substituted 2-[2-(Diphenylmethylene)hydrazinyl]-5,5-dimethyl-4-oxohex-2-enoates

et al. 2021

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Synthesis and Biological Activity of N-Aryl(alkyl)-2-[2-(9H-fluoren-9-ylidene)hydrazinylidene]-5,5-dimethyl-4-oxohexanamides

et al. 2019

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Chemistry of iminofuran: VIII. Recyclization of 5-aryl-3-arylimino-3H-furan-2-ones effected by cyanoacetic acid derivatives

et al. 2013

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Chemistry of iminofurans: VI.* Synthesis and structure of 2-(2-ylidenehydrazino)-substituted 4-aryl-4-oxobut-2-enoic and 5,5-dimethyl-4-oxohex-2-enoic acids

Cited by 9 publications

References 5 publications

Synthesis and Biological Activity of Substituted 2-[2-(Diphenylmethylene)hydrazinyl]-5,5-dimethyl-4-oxohex-2-enoates

Synthesis and Biological Activity of Substituted 2-[2-(Diphenylmethylene)hydrazinyl]-5,5-dimethyl-4-oxohex-2-enoates

Synthesis and Biological Activity of N-Aryl(alkyl)-2-[2-(9H-fluoren-9-ylidene)hydrazinylidene]-5,5-dimethyl-4-oxohexanamides

Chemistry of iminofuran: VIII. Recyclization of 5-aryl-3-arylimino-3H-furan-2-ones effected by cyanoacetic acid derivatives

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