Yuri Shafran

Yuri Shafran
Ural Federal University | UrFU · Department of Organic Chemistry (Chemical Technology)

PhD

About

65
Publications
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645
Citations

Publications

Publications (65)
Article
Full-text available
Here, we report that the reaction of enaminones, from a class of azole series, with sulfonyl azides leads to a difficult-to-separate mixture of two pairs of compounds: (1) 4-azoloyl-NH-1,2,3-triazoles with sulfonamides and (2) azolyl diazoketones with N-sulfonamidines, as a result of the implementation of two competing reactions. On one hand, the e...
Article
N‐(2‐Substituted benzyl)‐2,5‐dimethoxyphenethylamines often cause severe poisonings which has led to their legal prohibition in many countries. At the same time, their positional isomers can be studied as potential therapeutic drugs. In this regard, the search for various approaches to differentiate these isomers is an important practical task, the...
Article
N‐(2‐Methoxybenzyl)‐2,5‐dimethoxyphenethylamines (NBOMes) are synthetic phenethylamine derivatives emerging on the drugs of abuse market and reported to be associated with untoward effects in people using drugs. The mechanism of action involves agonism at serotonin 5‐HT2A receptors affecting cognitive and behavioral processes. At the same time, cer...
Article
Novel water-soluble sulfonyl azides were synthesized, which are basic by nature. The obtained compounds were used as donors of the diazo group in the diazo transfer reaction. Due to their good solubility in water and high polarity, the byproducts formed in this case were easily separated from the desired products by washing with water or column chr...
Article
Synthesis of 4-acetyl-substituted azoles (1,2,3-triazole, 1,2,3-thiadiazole, and 1,2-oxazole) is reported. Organocatalytic reactions of 4-acetyl-1,2,3-triazoles with aryl azides were used to obtain bis-1,2,3-triazoles containing directly linked ring systems. The reactions of 4-acetylazoles with DMF–DMA led to the formation of enamines. It was found...
Article
Reactions of thioamides with nitrogen-rich 1,3-dipoles, diazo compounds and azides, have been known for long time already. However in recent years introduction of catalysts of different types (rhodium-, ruthenium- and copper-containing and Lewis acids) as well as highly electrophilic sulfonyl azides, allowed the development of new methods for the s...
Chapter
The chapter is focused on the synthesis of 1,2,3-thiadiazoles including Hurd-Mori reaction, Wolff approach, and oxidative cyclization of hydrazones bearing thioamide group. It also contains data on the synthesis of fused 1,2,3-thiadiazoles and those linearly connected to other heterocycles. Moreover, a short overview of biological properties is giv...
Article
Full-text available
A new approach towards the synthesis of multisubstituted thiophenes is elaborated based on Rh(II)-catalyzed domino reactions of acyclic diazoesters with α-cyanothioacetamides. It provides a way for the preparation of 5-amino-3-(alkoxycarbonylamino)thiophene-2-carboxylates, 2-(5-amino-2-methoxycarbonylthiophene-3-yl)aminomalonates and (2-cyano-5-ami...
Data
NMR spectra of all new compounds and data of X-ray analysis.
Data
Experimental procedures and characterization data of all new compounds.
Article
Full-text available
Differentiation of new psychoactive substance (NPS), 6-(2-methylaminopropyl)benzofuran (6-MAPB), and its positional isomer, 2-(2-methylaminopropyl)benzofuran (2-MAPB), by means of gas chromatography/mass spectrometry (GC/MS) with quadrupole detection is ambiguous. Reliable distinguishing of the two isomers could be achieved by MS/MS spectra recorde...
Article
Full-text available
Synthetic cannabinoids are one of the most rapidly expanding classes of novel psychoactive substances found in illegal markets. These substances have evolved to the point that many examples no longer fit with the traditional cannabinoid classification system, where assignment of these compounds is difficult and ambiguous, leading to inconsistencies...
Article
[Figure not available: see fulltext.] 2-(1,2,3-Thiadiazol-5-yl)enamines and 3-(1,2,3-triazol-4-yl)enaminones react with arylhydroxamoyl chlorides at room temperature with the exclusive formation of 3-aryl-4-(1,2,3-thiadiazol-5-yl)- and [4-(1,2,3-triazol-4-yl)carbonyl]isoxazoles in high yields. The proposed mechanism includes in situ generation of n...
Article
The synthesis of a new series of 2-aryl-5-amino-1,2,3-triazole derivatives is reported. The photochemical properties of these new fluorophores were studied both experimentally and using theoretical models. The compounds were found to be fluorescent, with Stokes shifts ranging from 40 nm (2494 ≿м−1) to 140 nm (9461 cm−1) and quantum yield values bet...
Article
Emergence of new psychoactive substances (NPS), hallucinogenic phenethylamines in particular, in illicit market is a serious threat to human health in global scale. We have detected and identified N-(2-methoxybenzyl)-2-(2,4,6-trimethoxyphenyl)ethanamine (2,4,6-TMPEA-NBOMe), a new compound in NBOMe series. Identification was achieved by means of gas...
Article
Illicit new psychoactive substances (NPS) are a serious threat to health throughout the world. Such NPS do not usually pass preliminary pharmacological trials. In 2014, we identified a series of five new synthetic cannabinoids with an indazole-3-carboxamide structure bearing an N-1-methoxycarbonylalkyl group. The compounds have very high cannabimim...
Article
Reactions of β-1,2,3-thiadiazol-5-yl enamines with acetyl chloride in 1,4-dioxane lead to the formation of either dienamines or novel thieno[2,3-d]pyridazines depending on the time and reaction temperature. Conditions were found for the selective synthesis of thieno[2,3-d]pyridazines. A plausible mechanism involves formation of C–S and C–C bonds an...
Article
Two directions for self-condensation of beta-(isoxazol-5-yl) enamines under treatment with either acetyl chloride or acids were found leading to new 1,3-diisoxazolyl-1,3-dieneamines and 1,3,5-triisoxazolyl benzenes. The effect of solvent, acid, temperature and the reaction time on the ratio of reaction products were investigated. Trans-E-cis config...
Article
By means of gas chromatography with high resolution mass spectrometry (GC-HRMS), ultra-high performance liquid chromatography in combination with high resolution tandem mass spectrometry (UHPLC-HRMS), nuclear magnetic resonance spectroscopy (NMR) and Fourier transform infrared spectroscopy (FT-IR), structure of a series from a novel synthetic canna...
Article
By means of gas chromatography with mass spectrometry detector (GC-MS), liquid chromatography-mass spectrometry (LC-MS) and nuclear magnetic resonance spectroscopy (NMR), structure of a series from a novel class of synthetic cannabimimetics bearing 2,2,3,3-tetramethylcyclopropanecarbonyl moiety was established. It was found that this fragment could...
Article
Full-text available
Novel self-condensation of 3-(azol-5-yl)-1,1-dimethylenamines has been found to form new C-C bonds leading to 2,4-(1,2,3-triazole-1,2,3-thiadiazole-3-phenylisothiazole)-(1E,3Z)-5-yl-butadiene-1-amines. The discovered reaction represents a new example of C-H functionalization in unsaturated systems and can serve an efficient synthetic approach to ra...
Article
New method for the study of reactivity of highly reactive compounds was proposed and applied to determine the effect of substituents in α-diazoacetamidines, and -imidates. The introduction of electron-releasing groups to the nitrogen atom of the amidine, and imidate functions was shown to increase the reactivity of the substances studied. The resul...
Article
Full-text available
Methods for the synthesis of condensed 1,2,3-triazoles, including mesoionic compounds, in the literature up to 2007 inclusively are presented. They are classified according to the method by which the molecular skeleton is formed. Mesoionic condensed compounds of the 1,2,3-triazole series are examined separately.
Article
Full-text available
A series of α-carbonyl diazoacetonitriles has been synthesized and subjected to reaction with hydrogen halides. The scope and limitations of this reaction for preparing 5-halo-1,2,3-triazoles have been determined. The experimental energy of this cyclization is 15-20 Kcal mol-1. A mechanism of this reaction consists of two steps-addition of HHa1 to...
Article
Full-text available
The rearrangement of 5-amino-1,2,3-thiadiazoles under the influence of halogen-containing oxidizing to bis(triazolyl) disulfides was observed. Ammonia reduces the disulfides obtained to 5-mercapto-1,2,3-triazoles.
Article
Full-text available
The information about the synthesis, chemical, physicochemical, and biological properties, and also the stereochemistry of ?-aminonitriles has been classified. The bibliography includes 283 references.
Article
Full-text available
The mass spectra of the negative ions of the dissociative resonance capture of electrons of diazo amides and the isomeric triazoles were studied. The molecular negative ions of these compounds are unstable and do not undergo interisomerization. The principal fragmentation process involves the elimination of a molecule of nitrogen and transformation...
Article
Full-text available
The behavior of the isomeric 5-amino-1,2,3-thiadiazoles and 5-mercapto-1,2,3-triazoles under electron impact was studied. It was shown that mass spectrometry can serve as a rapid and reliable method for the identification of these compounds. Key factors in the assignment of a compound to one or the other class are the peaks of the [M-N2]+ ions, whi...
Article
Diazomalondiamid (II) reagiert mit den Aminen (Ia) und (Ib) zu den Hydroxytriazol-Salzen (III), aus denen mit verdünnten Säuren das Hydroxytriazol (IV) freigesetzt wird.
Article
Die α-Diazo-a-cyanoessigsäurederivate (Ia)-(Ic) bzw. das Keton (Id) cyclisieren mit Schwefelwasserstoff in Gegenwart von Triethylamin zu den 5-Amino-1,2,3-thiadiazolen (II), die mit Ammoniak oder Methylamin beim Erhitzen zu den Mercaptotriazolen (III) isomerisieren.
Article
Full-text available
An analysis of the electron impact mass-spectra of 2-diazo-2-cyanoacetamides and the 4-cyano-5-hydroxy-1,2,3-triazoles isomeric to them, showed that the molecular ions of these compounds do not isomerize one into another. The diazo compounds decompose, undergoing a Wolff rearrangement. To study the fragmentation of the diazoamides, one can use the...
Article
Full-text available
1,2,3-Triazol-5-olates are formed in the reaction of diazomalonodiamide and 2-diazo-2-cyanoacetic acid amide and N-methylamide with sodium ethoxide, triethylamine, and ammonia. The products of the reaction of 2-diazo-2-cyanoacetamide with primary amines are mixtures of 4-cyano-1,2,3-triazol-5-olates and 5-amino-1-alkyl-1,2,3-triazole-4-carboxamides...
Article
The reaction of carbonyl derivatives of diazoacetonitrile with hydrogen sulfide in the presence of triethylamine yields 4-substituted 5-amino-1,2,3-triadiazoles. Under analogous conditions, hydrogen selenide and ethyl mercaptan reduce the starting diazo compounds to hydrazones. Thiadiazoles are recyclized to 4-substituted 5-mercapto-1,2,3-triazoles...
Article
We have observed that 5-amino-l,2,3-thiadiazole-4-carbothioamide derivatives la,b are al- so converted to 5-mercapto-l,2,3-triazoles under these conditions. However, in contrast to the re6yclization described above, this process takes place with the participation of the ni- trogen atom of the carbothioamide group and leads to thioamides lla,b rathe...
Article
Full-text available
Carbonyl-substituted derivatives of diazoacetonitrile have been obtained by the diazotization of amines and by diazo-group transfer which, under the action of hydrogen halide, have been converted into 4-carbonyl-substituted 5-halo-1H-1,2, 3-triazoles. The structures of these compounds have been confirmed by mass spectrometry and independent synthes...
Article
The reactions of 4-chloroimidazo[4,5-d]-1,2,3-triazine with a number of nucleophilic reagents have been studied. Either replacement of the chlorine atom in position 4 of the 1,2,3-triazine ring or opening of the triazine ring with the formation of products of the interaction of the intermediate 5-diazoimidazole-4-carbonitrile with these nucleophile...
Article
Die Diazo-cyanessigsäurederivate (I) reagieren mit Chlorwasserstoff unter Cyclisierung zu 5-Chlortriazolen (II) bzw. mit Schwe-felwasserstoff zu Thiadiazolen (III).
Article
Aus dem Nitril (I) erhält man in bekannter Weise den Imino-ester (II) und aus diesem die Amidine (III).

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