scholarly journals Synthesis of 5-aryl-4-acyl-3-hydroxy- 1-carboxymethyl-3-pyrrolin-2-ones

2020 ◽  
Vol 64 (11) ◽  
pp. 9-12
Author(s):  
Vladimir L. Gein ◽  
◽  
Evgenia V. Pastukhova ◽  
Keyword(s):  
Nmr Spectroscopy ◽  
Carbonyl Group ◽  
1H Nmr ◽  
1H Nmr Spectroscopy ◽  
Spectral Characteristics ◽  
Alcoholic Solution ◽  
Biologically Active ◽  
Acyl Residue ◽  
Reaction Products ◽  
Three Component Reaction

5-Aryl-1,4-disubstituted terahydropyrrole-2,3-diones are five-membered nitrogen heterocycles containing in the first alkyl position or an aryl functionalized substituent and in the fourth position in another state of nature an acyl residue. Trahydropyrrole-2,3-diones constitute a significant class of available and stable substances. Along with this, they easily enter into reactions with various nucleophilic reagents due to the highly reactive carbonyl group in the third position of the heterocycle. The presence of the latter, as well as the carbonyl group of the side chain, makes it possible to form various condensed systems from heterocycles in reactions with binucleophilic reagents. The synthesis of biologically active substances based on 1,4,5-trisubstituted tetrahydropyrrole-2,3-diones is one of the promising ways of using this class of compounds. Previously, it was found that 1,4,5-trisubstituted 3-hydroxy-3-pyrin-2-ones have anti-inflammatory, analgesic, antimicrobial, nootropic, antiplatelet and antiviral activity. We set the task to obtain 5-aryl-4-acyl-3-hydroxy-3-pyrrolin-2-ones, in the first position of the heterocycle there is a carboxymethyl substituent. By setting up a three-component reaction of acylpyruvic acid ether with aromatic aldehydes and glycine in dioxane in dioxane. The structure of the compound was established on the basis of IR and 1H NMR spectroscopy data. Based on the data of 1H NMR spectroscopy and a positive reaction with an alcoholic solution of iron(III) chloride, the predominant presence of compounds in the enol form was established. The article presents the proposed mechanism and schemes of the formula for the synthesis of 5-aryl-4-acyl-3-hydroxy-1-carboxymethyl-3-pyrrolin-2-ones, their physicochemical and spectral characteristics, as well as the yields of the reaction products.

scholarly journals Synthesis and properties of 1-aminocarbonylmethyl-5-aryl- 4-aroyl-3-hydroxy-3-pyrroline-2-ones

2020 ◽  
Vol 64 (10) ◽  
pp. 28-32
Author(s):  
Vladimir L. Gein ◽  
◽  
Evgenia V. Pastukhova ◽  
Keyword(s):  
Acetic Acid ◽  
Nmr Spectroscopy ◽  
Physicochemical Properties ◽  
Hydrazine Hydrate ◽  
1H Nmr ◽  
1H Nmr Spectroscopy ◽  
Glacial Acetic Acid ◽  
Spectral Characteristics ◽  
Biologically Active ◽  
Three Component Reaction

3-Hydroxy-3-pyrrolin-2-ones are fully hydrogenated heterocyclic compounds, the base of which is included in a number of biologically active substances and drugs. Scientists' interest in 3-Hydroxy-3-pyrrolin-2-ones is due to the fact that, with their availability and high stability, they also have high reactivity due to the active carbonyl group in the third position of the heterocycle and easily interact with moconucleophiles. In addition, the presence of acyl and ethoxycarbonyl groups in the fourth position of the heterocycle makes it possible to obtain various condensed systems in reactions with binucleophiles, thereby making it possible to expand the range of the indicated compounds. We set the task to prepare 5-aryl-4-acyl-3-hydroxy-3-pyrrolin-2-ones containing an amino-carbonylmethyl substituent in the first position of the heterocycle, which were not previously described in the literature. It was also supposed to establish how the obtained compounds react with hydrazine hydrate. A series of 1-aminocarbonylmethyl-5-aryl-4-aroyl-3-hydroxy-3-pyrrolin-2-ones was obtained by setting up a three-component reaction of aroylpyruvic acid methyl ester with aromatic aldehydes and glycinamide hydrochloride in glacial acetic acid. The structure of the obtained compounds was established on the basis of IR and 1H NMR spectroscopy data. Based on the data of 1H NMR spectroscopy and a positive reaction with an alcoholic solution of iron(III) chloride, the predominant existence of the obtained compounds in the enol form was established. The article describes the mechanism of three-component reactions, the structural formulas of the obtained compounds, their physicochemical properties and spectral characteristics, as well as the yields of the reaction products. We have also studied the interaction of 1-substituted 5-aryl-4-acyl-3-hydroxy-3-pyrrolin- 2-ones with such a binucleophilic reagent as hydrazine hydrate. As a result of refluxing 1-amino-carbonylmethyl-3-hydroxy-4-(4-methoxybenzoyl)-5-(2-chlorophenyl)-3-pyrrolin-2-one and hydrazine hydrate in glacial acetic acid, 2-[4-(2-chlorophenyl)-3-(4-methoxyphenyl)-6-oxo-4,6-dihydropyrrolo [3,4-c] pyrazol-5(1H)-yl] acetamide. The article describes the proposed reaction mechanism, product yield, its physicochemical properties and spectral characteristics.

scholarly journals 1H-NMR Spectroscopy of Body Fluids: Inborn Errors of Purine and Pyrimidine Metabolism

1999 ◽  
Vol 45 (4) ◽  
pp. 539-548 ◽  
Author(s):  
Ron A Wevers ◽  
Udo FH Engelke ◽  
Sytske H Moolenaar ◽  
Christa Bräutigam ◽  
Jan GN de Jong ◽  
...  
Keyword(s):  
Nmr Spectroscopy ◽  
1H Nmr ◽  
1H Nmr Spectroscopy ◽  
Spectral Characteristics ◽  
Sample Volume ◽  
Body Fluids ◽  
Operating Conditions ◽  
Urine Samples ◽  
Pyrimidine Metabolism ◽  
Inborn Errors

Abstract Background: The diagnosis of inborn errors of purine and pyrimidine metabolism is often difficult. We examined the potential of 1H-NMR as a tool in evaluation of patients with these disorders. Methods: We performed 1H-NMR spectroscopy on 500 and 600 MHz instruments with a standardized sample volume of 500 μL. We studied body fluids from 25 patients with nine inborn errors of purine and pyrimidine metabolism. Results: Characteristic abnormalities could be demonstrated in the 1H-NMR spectra of urine samples of all patients with diseases in the pyrimidine metabolism. In most urine samples from patients with defects in the purine metabolism, the 1H-NMR spectrum pointed to the specific diagnosis in a straightforward manner. The only exception was a urine from a case of adenine phosphoribosyl transferase deficiency in which the accumulating metabolite, 2,8-dihydroxyadenine, was not seen under the operating conditions used. Similarly, uric acid was not measured. We provide the 1H-NMR spectral characteristics of many intermediates in purine and pyrimidine metabolism that may be relevant for future studies in this field. Conclusion: The overview of metabolism that is provided by 1H-NMR spectroscopy makes the technique a valuable screening tool in the detection of inborn errors of purine and pyrimidine metabolism.

scholarly journals Synthesis, physic and chemical properties of 2-(4-R-5-(thiophene-2-ylmethyl)-4h-1,2,4-triazole-3-ylthio)acetate acids and their salts

2018 ◽  
pp. 48-54
Author(s):  
O. A. Suhak ◽  
О. I. Panasenko ◽  
Ye. G. Knysh
Keyword(s):  
Biological Activity ◽  
Nmr Spectroscopy ◽  
1H Nmr ◽  
1H Nmr Spectroscopy ◽  
Chemical Properties ◽  
Biological Action ◽  
Biologically Active ◽  
Physico Chemical ◽  
Methods Of Synthesis ◽  
Medicinal Drugs

Derivatives of 1,2,4-triazole are inherent in various types of biological activity. They can be used as pesticide and medicinal drugs (anticonvulsants, analgetics, antitumor and antibacterial). In this regard the search of new methods of synthesis and investigation of biological activity of 2-(4-R-5-(thiophene-2-ylmethyl)-4H-1,2,4-triazole-3-ylthio)acetate acids and their salts is relevant nowadays. With the aim of finding the new biologically active compounds 2-(4-R-5-(thiophene-2-ylmethyl)-4H-1,2,4-triazole-3-ylthio)acetate acids and their salts are synthesized, where R is methyl, ethyl, phenyl. The interaction of 4-R-5-(thiophene-2-ylmethyl)-4H-1,2,4-triazole-3-thions with monochloracetate acid in the medium of i-propyl alcohol in the presence of an equivalent amount of alkali the corresponding 2-(4-R-5-(thiophene-2-ylmethyl)-4H-1,2,4 triazole-3-ylthio)acetate acids are obtained on the basis of which the corresponding salts of morpholine, dimethylamine, monoethanolamine, pteridine, ZnSO4 , CuSO4, NaOH and KOH are obtained and the structure of the received compounds was confirmed on the basis of the data of elemental, IR-, 1H-NMR-spectroscopy. The synthesis of 2-(4-R-5-(thiophene-2-ylmethyl)-4H-1,2,4-triazole-3-ylthio) acetate acids and their salts was conducted. With the help of modern physico-chemical methods: elemental analysis, IR, 1H-NMR-spectroscopy the structure of synthesized compounds, and their individuality by HPLC-MS is proved. In the IR spectrum of the compound 2-(4-phenyl-5-(thiophene-2-ylmethyl)-4H-1,2,4-triazole-3-ylthio)acetate acid Ic available band fluctuations groups characteristic for the nucleus of 1,2,4-triazole: NH– in the range of 3 400–3 100 cm-1,–C=N– – 1 690–1 620 cm-1. Also present band fluctuations groups –C–S– at 691 cm-1. Available band fluctuations characteristic of the group –CH2 within 1496.59 cm-1 and group –COO-H– – 1722.70 cm-1. This suggests the possibility to further study the biological action of the synthesized compounds.

scholarly journals Identification and Quantitation of Ursolic and Oleanolic Acids in Ilex aquifolium L. Leaf Extracts Using 13C and 1H-NMR Spectroscopy

Molecules ◽  
2019 ◽  
Vol 24 (23) ◽  
pp. 4413
Author(s):  
Doreen Palu ◽  
Ange Bighelli ◽  
Joseph Casanova ◽  
Mathieu Paoli
Keyword(s):  
Nmr Spectroscopy ◽  
1H Nmr ◽  
13C Nmr ◽  
1H Nmr Spectroscopy ◽  
Limit Of Detection ◽  
Biologically Active ◽  
Leaf Extracts ◽  
Simple Method ◽  
Ilex Aquifolium ◽  
Limit Of Quantitation

Leaves of Ilex aquifolium L. have been used for their therapeutic properties. In previous studies, components contained in the leaves were first isolated by various chromatographic techniques. Then, quantitation of oleanolic and ursolic acids, which are responsible for the biological and therapeutic activities of the plant, was performed by HPLC, HPTLC, and somewhat by GC-MS. Our objective was to develop a simple method that allows the identification of compounds contained in the leaves of Corsican I. aquifolium and to quantify ursolic and oleanolic acids. Leaves were successively extracted with hexane and dichloromethane. The extracts were chromatographed on silica gel and the fractions of column chromatography submitted to 13C-NMR analysis, following a computerized method developed in the laboratory. 13C-NMR allowed the identification of various triterpenes including ursolic acid and oleanolic acid. Quantitation of both acids was achieved, for the first time, by 1H-NMR after validation of the method (accuracy, precision, linearity, limit of detection and limit of quantitation). Ursolic and oleanolic acids accounted for 55.3% and 20.8% of the dichloromethane extract, respectively. This represents 1.3% and 0.5% of the mass of dried leaves. 1H-NMR spectroscopy appeared as a powerful tool for a rapid quantitation of biologically active compounds from I. aquifolium.

Asymetrical Dimer - allyl-palladiu Complexes II. Data from Infrared Spectra and Chemical Behaviour

2008 ◽  
Vol 59 (7) ◽  
Author(s):  
Maria Maganu ◽  
Filip Chiraleu ◽  
Constantin Draghici ◽  
Gheorghe Mihai
Keyword(s):  
Carbon Monoxide ◽  
Nmr Spectroscopy ◽  
1H Nmr ◽  
Infrared Spectra ◽  
Analytical Methods ◽  
1H Nmr Spectroscopy ◽  
Chemical Behaviour ◽  
The Asymmetry ◽  
Pd Complexes

The previous data obtained by 1H-NMR spectroscopy established the existence of an asymmetry of the bond between Pd and p-allylic groups, even in the p-allyl-Pd complexes dimers which are considered usually symmetric dimers. The asymmetry of the bond depends by the substitutes of the allylic group. Other analytical methods were investigated for additional proof of the obtained results. Thus, this paper discusses how this asymmetry would be reflected in the infrared spectra and in the reaction of the complexes with carbon monoxide.

Diastereoselective Reduction of Selected α-substituted β-keto Esters and the Assignment of the Relative Configuration by 1H-NMR Spectroscopy

2020 ◽  
Vol 07 ◽  
Author(s):  
Christian Trapp ◽  
Corinna Schuster ◽  
Chris Drewniok ◽  
Dieter Greif ◽  
Martin Hofrichter
Keyword(s):  
Nmr Spectroscopy ◽  
1H Nmr ◽  
1H Nmr Spectroscopy ◽  
Selective Reduction ◽  
Reducing Agents ◽  
Relative Configuration ◽  
Curtius Rearrangement ◽  
Keto Esters ◽  
Hydroxy Esters ◽  
Diastereoselective Reduction

Background:: Chiral β-hydroxy esters and α-substituted β-hydroxy esters represent versatile building blocks for pheromones, β-lactam antibiotics and 1,2- or 1,3-aminoalcohols. Objective:: Synthesis of versatile α-substituted β-keto esters and their diastereoselective reduction to the corresponding syn- or anti-α-substituted β-hydroxy esters. Assignment of the relative configuration by NMR-spectroscopy after a CURTIUS rearrangement of α-substituted β-keto esters to 4-substituted 5-methyloxazolidin-2-ones. Method:: Diastereoselective reduction was achieved by using different LEWIS acids (zinc, titanium and cerium) in combination with complex borohydrides as reducing agents. Assignment of the relative configuration was verified by 1H-NMR spectroscopy after CURTIUS-rearrangement of α-substituted β-hydroxy esters to 4-substituted 5-methyloxazolidin-2-ones. Results:: For the syn-selective reduction, titanium tetrachloride (TiCl4) in combination with a pyridine-borane complex (py BH3) led to diastereoselectivities up to 99% dr. High anti-selective reduction was achieved by using cerium trichloride (CeCl3) and steric hindered reducing agents such as lithium triethylborohydride (LiEt3BH). After CURTIUS-rearrangement of each α-substituted β-hydroxy ester to the corresponding 4-substituted 5-methyloxazolidin-2-one, the relative configuration was confirmed by 1H NMR-spectroscopy. Conclusion:: We have expanded the procedure of LEWIS acid-mediated diastereoselective reduction to bulky α-substituents such as the isopropyl group and the electron withdrawing phenyl ring.

Conformational study on ribonucleoside O-phosphonylmethyl derivatives by 1H NMR spectroscopy

1985 ◽  
Vol 50 (8) ◽  
pp. 1899-1905 ◽  
Author(s):  
Milena Masojídková ◽  
Jaroslav Zajíček ◽  
Miloš Buděšínský ◽  
Ivan Rosenberg ◽  
Antonín Holý
Keyword(s):  
Nmr Spectroscopy ◽  
1H Nmr ◽  
1H Nmr Spectroscopy ◽  
Conformational Study ◽  
H Nmr ◽  
Conformational Properties

Conformational properties of ribonucleoside 5'-O-phosphonylmethyl derivatives have been determined by 1H NMR spectroscopy and compared with those of natural nucleosides and 5'-nucleotides.

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