Reactions of N'-[2-Oxo-5-R-furan-3(2H)-ylidene]acylhydrazides with Primary and Secondary Alcohols

Kizimova, I. A.; Игидов, Н. М.; Kiselev, M. A.; Иванов, Дмитрий Владимирович; Syutkina, A. I.

doi:10.1134/s1070363220050096

Cited by 9 publications

(4 citation statements)

References 8 publications

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“…Form B is characterized by the presence in the spectrum of a doublet of protons of the CH2 group at 3.30-3.44 and 3.20-3.39 ppm, and for form C, singlets of the NH protons (13.04-13.83 ppm) and CH2 (3.80-4.42 ppm). The spectral data of compounds 3a-h are in good agreement with the corresponding spectral data of alkyl 4-oxo-4-aryl-2-[2-(arylcarbonyl)hydrazinylidene]butanoates, which have a similar structure and also exist in three forms [37].…”

Section: Resultssupporting

confidence: 77%

Synthesis, intramolecular cyclization and anti-inflammatory activity of substituted 2-(2-(Furan-2-carbonyl)hydrazono)-4-oxobutanoic Acids

Igidov¹,

Lipin²,

Turyshev³

et al. 2022

Chim.Tech.Acta

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A method was proposed for the synthesis of substituted 2-(2-(furan-2-carbonyl)hydrazono)-4-oxobutanoic acids by the reaction of substituted 2,4-dioxobut-2-enoic acids with furan-2-carbohydrazide. It was found that substituted 2-(2-(furan-2-carbonyl)hydrazono)-4-oxobutanoic acids undergo intramolecular cyclization in the presence of propionic anhydride to form the corresponding N'-(2-oxofuran-3(2H)-ylidene)furan-2-carbohydrazides. The anti-inflammatory activity of the obtained compounds was studied. It was found that the obtained compounds have pronounced anti-inflammatory activity.

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Section: Resultssupporting

confidence: 77%

Synthesis, intramolecular cyclization and anti-inflammatory activity of substituted 2-(2-(Furan-2-carbonyl)hydrazono)-4-oxobutanoic Acids

Igidov¹,

Lipin²,

Turyshev³

et al. 2022

Chim.Tech.Acta

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“…Also, we showed that N′-[5-aryl-2-oxofuran-3(2Н)ylidene]furan-2-carbohydrazides and its precursor 4aryl-2-[2-(furan-2-ylcarbonyl)hydrazinylidene] -4oxobutanoic acids have analgesic activity in the previous studies [55]. The interaction of 3-hydrazinylidenefuran-2(3H)-one with alcohols in the presence of triethylamine, which leading to the formation of a mixture of alkyl 2hydrazinylidene-4-oxobutanoates and alkyl 5-hydroxy-4,5dihydro-1H-pyrazole-3-carboxylates, was described earlier [56] (Scheme 1). In the this study, the research into the reactivity of 3-hydrazinylidenefuran-2(3H)-one towards alcohols was continued.…”

Section: Introductionmentioning

confidence: 96%

Synthesis, recyclization under the action of methanol and analgetic activity of N'-(5-aryl-2-oxofuran-3(2H)-ylidene)furan-2-carbohydrazides

et al. 2022

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New methyl 5-aryl-1-(furan-2-carbonyl)-1H-pyrazole-3-carboxylates were obtained via decyclization reaction of N'-(5-aryl-2-oxofuran-3(2H)-ylidene)furan-2-carbohydrazides under the action of methanol. Starting N'-(5-aryl-2-oxofuran-3(2H)-ylidene)furan-2-carbohydrazides were obtained by intramolecular cyclization of substituted 4-aryl-2-[2-(furan-2-ylcarbonyl)hydrazinylidene]-4-oxobutanoic acids in propionic anhydride. The structure of the compounds obtained was confirmed by the 1H NMR spectroscopy, IR spectrometry and elemental analysis methods. Analgesic activity of some obtained compounds was studied by the “hot plate” method on outbred white mice of both sexes with intraperitoneal injection.

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“…3-Imino(hydrazono)-3H-furan-2-ones have several reactive centers in its structure, due to which it becomes possible to change the direction of the attacking reagent, depending on the nature of the substituents in the furan cycle and imino(hydrazono)function. 3-Imino(hydrazono)-3H-furan-2-ones are easily subjected to decyclyzation reactions when attacking NH-and OH-nucleophiles on the lactone carbonyl [20,21]. Under the action of CH-nucleophiles on the 3-imino(hydrazono)-3H-furan-2-one ring the recyclization reaction proceeds to form pyrrole derivatives [22,23].…”

Section: Introductionmentioning

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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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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Reactions of N'-[2-Oxo-5-R-furan-3(2H)-ylidene]acylhydrazides with Primary and Secondary Alcohols

Cited by 9 publications

References 8 publications

Synthesis, intramolecular cyclization and anti-inflammatory activity of substituted 2-(2-(Furan-2-carbonyl)hydrazono)-4-oxobutanoic Acids

Synthesis, intramolecular cyclization and anti-inflammatory activity of substituted 2-(2-(Furan-2-carbonyl)hydrazono)-4-oxobutanoic Acids

Synthesis, recyclization under the action of methanol and analgetic activity of N'-(5-aryl-2-oxofuran-3(2H)-ylidene)furan-2-carbohydrazides

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

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