Synthesis of 5-hydroxy- and 5-acylhydrazinopyrazolidines by the reaction of ?-substituted hydrazides with ?,?-unsaturated aldehydes and their biological activity

Зеленин, K. Н.; Dovgilevich, A. V.; Bezhan, I. P.; Golubeva, G. A.; Свиридова, Л. А.; Pastushenkov, L. V.; Gromova, É. G.; Gatchina, T. A.; Pomogaibo, S. V.

doi:10.1007/bf00514307

Cited by 6 publications

(3 citation statements)

References 6 publications

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“…trans-1-Acetyl-5-hydroxy-3-methyl-2-phenylpyrazolidine was obtained by the method of [4]. trans-1-Acetyl-3-methyl-5-nitromethyl-2-phenylpyrazolidine (1).…”

Section: Methodsmentioning

confidence: 99%

Synthesis of new functional derivatives of pyrazolidine from 1-acetyl-3-methyl-5-nitromethyl-2-phenylpyrazolidine

Свиридова

Golubeva

Shorunov

2006

Chem Heterocycl Compd

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3-Nitromethylpyrazolidine reacts with derivatives of unsaturated acids and reducing agents with the formation of polyfunctional compounds of the pyrazolidine nucleus.We previously found a new method of directly introducing CH-acid radicals into the pyrazolidine molecule [1] on the surface of adsorbents without a solvent. Among others, a method of synthesizing pyrazolidine 5-nitromethyl derivatives was developed. In the present work further conversions of 1-acetyl-3-methyl-5-nitromethyl-2-phenylpyrazolidine (1) have been studied using the reactivity of both the methylene and the nitro groups.In [1] conditions were found for the synthesis of nitro derivative 1 with a cis:trans isomers ratio of 1:4. After a small change to the method we succeeded in obtaining a diastereoselective course for the process on neutral aluminum oxide and the isomer ratio of compound 1 was ~1:100 according to data of 1 H NMR spectra. In this way we obtained predominantly one diastereomeric pair of trans structure. Attempts to introduce the obtained nitro derivative 1 into a Michael reaction with derivatives of unsaturated acids under the usual conditions with a basic catalyst (triethylamine) were unsuccessful. In view of our positive experiment using the method of carrying out the reaction on the surface of an adsorbent without a solvent [1], we carried out a series of trial experiments and discovered that the Michael reaction with acrylonitrile proceeds best of all at room temperature on basic aluminum oxide containing 20% adsorbed KF. After 48 h the initial compound 1 reacted completely with the formation of product 2 by addition of two molecules of acrylonitrile. N N Me Ac Ph NO 2 N N Me Ac Ph O 2 N R R N N Me Ac Ph O 2 N R R 1 + 2, 3a 3b,c 1 2 R = CN; 3a-c R = COOMe; b R 1 = H; c R 1 = Me __________________________________________________________________________________________ 1 Moscow M. V

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“…trans-1-Acetyl-5-hydroxy-3-methyl-2-phenylpyrazolidine was obtained by the method of [4]. trans-1-Acetyl-3-methyl-5-nitromethyl-2-phenylpyrazolidine (1).…”

Section: Methodsmentioning

confidence: 99%

Synthesis of new functional derivatives of pyrazolidine from 1-acetyl-3-methyl-5-nitromethyl-2-phenylpyrazolidine

Свиридова

Golubeva

Shorunov

2006

Chem Heterocycl Compd

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“…[1,5,[7][8][9] For the last fifty years, there have been few articles about the synthesis of hydroxyl isoxazolidines from unsaturated carbonyl compounds and hydroxylamine (or its derivatives/ analogs). [4,5,[17][18][19][20][21][22][23][24][25][26][27][28][29] The formation of 5-hydroxyisoxazolidines easily occurred in neutral pH at room temperature (in rather an anhydrous condition), few examples of 3-hydroxyisoxazolidines synthesis are also known, but only for benzohydroxyamic acid and its analogs (p-NO 2 , p-Br and 2,3,5-(CH 3 ) 3 ). Hydroxy isoxazolidines are rather unstable (decompose when exposed to light and upon heating) and undergo chain-ring tautomerism.…”

Section: Introductionmentioning

confidence: 99%

A Simple Environmentally Friendly Method for the Synthesis of Hydroxyisoxazolidine Derivatives

et al. 2022

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A series of 5-hydroxyisoxazolidines has been successfully synthesized through tris(hydroxymethyl)aminomethane (TRIS) buffered hydroxylamine hydrochloride and α, βunsaturated ketones reaction. This synthetic approach can be considered as environmentally friendly because of the use of non-toxic and non-hazardous reagents at room temperature. The reaction is also metal-free and generates minimum non-toxic waste. The structure of 5-hydroxyisoxazolidines was confirmed not only by extended NMR analysis but by a series of elimination and acetylation reactions. Hydroisoxazolidines are obtained as a mixture of diastereomers (cis-, trans-and N-invertomers). Usually, three sets of 1 HNMR signals are observed for that class of compound (especially for protons H3 and both H4). The analysis of cis-and trans-isomerization of the product 2 b has been conducted.

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“…Starting 5-hydroxypyrazolidine 1 was prepared from 1-acetyl-2-phenylhydrazine and acroleine. 6 Aminopyrazoles 2a-c were obtained using a published procedure. 7 1 H and 13 C NMR spectra were measured on a VXR-400 Varian spectrometer in CDCl 3 solutions.…”

mentioning

confidence: 99%

Noncyclic intermediate in the synthesis of pyrazolidinylpyrazoles

Dlinnykh

Golubeva

Terentiev

et al. 2003

Mendeleev Communications

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Synthesis of 5-hydroxy- and 5-acylhydrazinopyrazolidines by the reaction of ?-substituted hydrazides with ?,?-unsaturated aldehydes and their biological activity

Cited by 6 publications

References 6 publications

Synthesis of new functional derivatives of pyrazolidine from 1-acetyl-3-methyl-5-nitromethyl-2-phenylpyrazolidine

Synthesis of new functional derivatives of pyrazolidine from 1-acetyl-3-methyl-5-nitromethyl-2-phenylpyrazolidine

A Simple Environmentally Friendly Method for the Synthesis of Hydroxyisoxazolidine Derivatives

Noncyclic intermediate in the synthesis of pyrazolidinylpyrazoles

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