88958-29-6Relevant academic research and scientific papers
Synthesis of 5-azolyl-2,4-dihydro-3H-1,2,4-triazole-3-thiones and 5-azolyl-1,3,4-thiadiazol-2-amines based on derivatives of 5-arylisoxazole-3-carboxylic and 4,5-dichloroisothiazole-3-carboxylic acids
Akishina, Ekaterina А.,Dikusar, Evgenij А.,Kurman, Peter V.,Nikitina, Eugeniya V.,Petkevich, Sergey K.,Potkin, Vladimir I.,Zaytsev, Vladimir P.,Zhukovskaya, Neliya А.
, p. 594 - 598 (2021/06/14)
[Figure not available: see fulltext.] 2-Mercapto-1,3,4-triazoles and 2-amino-1,3,4-thiadiazoles were synthesized by successive transformations of 5-arylisoxazole- and 4,5-dichloroisothiazole-3-carboxylic acids and their derivatives. The amino group of 5-(
The synthesis of isoxazolyl- and isothiazolylcarbamides exhibiting antitumor activity
Potkin,Petkevich,Kletskov,Zubenko,Kurman,Pashkevich,Gurinovich,Kulchitskiy
, p. 1667 - 1676 (2015/02/02)
Accessible 5-phenyl(p-tolyl)isoxazol-3-carboxylic, 4,5-dichlorothiazol-3-carboxylic and 5-(benzylsulfanyl)-4-chlorothiazol-3-carboxylic acids were converted via a series of cascade transformations into the corresponding (1,2-azolyl)-3-carbonyl azides whose reaction with slightly basic aryl(heteryl)amines led to generation of 1-(1,2-azolyl)-3-aryl(heteryl)carbamides. To obtain isoxazolyl(isothiazolyl)carbamides containing the residues of highly basic amines, (1,2-azolyl)-3-carbonyl azides were preliminary transformed into aryl (1,2-azol-3-yl)carbamates by the action of phenol or 4-fluorophenol. Carbamates then were introduced into reaction with aliphatic or heterocyclic amines. Some of the obtained compounds and their precursors show high antitumor activity and are capable to increase the effect of cytostatic drugs applied in the medical practice.
Synthesis of functionally substituted isoxazole and isothiazole derivatives
Potkin,Petkevich,Kletskov,Dikusar,Zubenko,Zhukovskaya,Kazbanov,Pashkevich
, p. 1523 - 1533 (2014/01/06)
Acylation of benzene and toluene with 5-phenyl- and 5-(p-tolyl)isoxazole-3- carbonyl chlorides gave 5-phenyl(or p-tolyl)isoxazol-3-yl phenyl(or p-tolyl)ketones which were reduced to the corresponding alcohols with sodium tetrahydridoborate in propan-2-ol. Selective reduction of the carboxy group in 4,5-dichloroisothiazole-3-carboxylic acid was achieved by the action of BH 3, and the aldehyde group in 4-formyl-2-methoxyphenyl 5-arylisoxazole-3-carboxylates and 4,5-dichloroisothiazole-3-carboxylates was reduced to hydroxymethyl group with sodium triacetoxyhydridoborate in benzene. Acylation of the resulting hydroxymethyl derivatives with 5-arylisoxazole- and 4,5-dichloroisothiazole-3-carbonyl chlorides afforded the corresponding esters containing two azole fragments in their molecules.
Mononuclear heterocyclic rearrangement of 5-arylisoxazole-3-hydroxamic acids into 3,4-substituted 1,2,5-oxadiazoles
Potkin, Vladimiri.,Petkevich, Sergeyk.,Lyakhov, Alexanders.,Ivashkevich, Ludmilas.
, p. 260 - 264 (2013/02/25)
By a series of successive transformations, 5-arylisoxazole-3-carboxylic acids (aryl=phenyl, p-tolyl, 2,5-dimethylphenyl) have been converted into 5-arylisoxazole-3-hydroxamic acids, which undergo rearrangement by the action of aqueous KOH to form 3,4-substituted 1,2,5-oxadiazoles. The structure of one of them, 1-(2,5-dimethylphenyl)-2-(4-hydroxy-1,2,5-oxadiazol-3-yl)ethanone, has been confirmed by single crystal X-ray analysis. Georg Thieme Verlag Stuttgart New York.
Synthesis of hydroxybenzaldehyde derivatives containing an isoxazole heteroring
Potkin,Gadzhily,Dikusar,Petkevich,Zhukovskaya,Aliev,Nagieva
, p. 127 - 136 (2012/05/20)
5-Phenyl(p-tolyl)isoxazole-3-carboxylic acids were synthesized starting from 3-hydroxyiminomethyl-5-phenyl(p-tolyl)isoxazoles, and their reactions with p-hydroxybenzaldehyde, vanillin, isovanillin, o-vanillin, and ethyl vanillin gave the corresponding esters. The latter were brought into condensation with aromatic amines to obtain Schiff bases which were reduced to amines. Pleiades Publishing, Ltd., 2012.
