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1.
O.G. Khudina E.V. Shchegol’kov M.I. Kodess A.N. Chekhlov O.A. Dyachenko O.N. Chupakhin 《Journal of fluorine chemistry》2005,126(8):1230-1238
The coupling of trifluoromethylated 1,3-diketones with (het)aryldiazonium chlorides results mainly in the formation of 1,2,3-triketones 2-(het)arylhydrazones while using hetarylamine with a NH-group at the α-position of the heterocycle as the diazonium component gives 4,7-dihydroazolo[5,1-c]triazines due to cyclization at the trifluoroacetyl fragment. Trifluoromethylated 1,2,3-triketones 2-(het)arylhydrazones and 7-hydroxy-4,7-dihydroazolo[5,1-c]triazines react regio-selectively with methyl hydrazine and phenyl hydrazine to form 3-CF3-pyrazoles. The long-range coupling constants (JF-H) of 1-methylpyrazoles and the chemical shifts of trifluoromethyl groups in the 19F NMR spectra can be used for the determination of regio-isomeric structures of mono(trifluoromethyl)-substituted pyrazoles. 2-(Het)arylhydrazones and 4,7-dihydroazolo[5,1-c]triazines with two trifluoromethyl substituents afford the mixtures of cis- and trans-azopyrazoles in the reactions with hydrazines. 相似文献
2.
O. G. Khudina Ya. V. Burgart V. I. Saloutin 《Russian Journal of Organic Chemistry》2017,53(10):1556-1563
The alkylation of ambident anions of 2-(methylsulfanyl)-6-(polyfluoroalkyl)pyrimidin-4(3H)-ones with 4-bromobutyl acetate leads to concurrent formation of O- and N-(4-acetoxybutyl) derivatives. Polar aprotic solvents favor formation of the O-isomer, and weakly polar dioxane favors N-alkylation. The reaction of 2-(methylsulfanyl)-6-(trifluoromethyl)pyrimidin-4(3H)-one with an equimolar amount of 1,2-dibromoethane in polar acetonitrile gives a mixture of N,N-, O,O-, and N,O-bridged bis-pyrimidines, as well as N- and O-[2-(methylsulfanyl)ethyl] derivatives, whereas in the presence of 10 equiv of 1,2-dibromoethane the N,O-isomer is formed as the only product. The reaction in weakly polar tetrahydrofuran yields N,N- and N,O-bispyrimidines. 相似文献
3.
A. E. Ivanova O. G. Khudina Ya. V. Burgart V. I. Saloutin M. A. Kravchenko 《Russian Chemical Bulletin》2011,60(11):2396-2400
Alkylation of polyfluoroalkyl-containing pyrazoles with 4-bromobutyl acetate in acetone in the presence of potassium carbonate leads to a mixture of isomeric 1-(4-acetoxybutyl)-3-fluoroalkyl- and 1-(4-acetoxybutyl)-5-fluoroalkylpyrazoles, which in a number of cases were successfully separated by HPLC. Deacylation in acidic medium with gaseous hydrogen chloride and in basic medium with gaseous ammonia leads to 1-(4-hydroxybutyl)pyrazoles, which manifest moderate tuberculostatic activity. 相似文献
4.
Khudina O. G. Ivanova A. E. Burgart Ya. V. Pervova M. G. Shatunova T. V. Borisevich S. S. Khursan S. L. Saloutin V. I. 《Russian Journal of Organic Chemistry》2019,55(6):782-791
Russian Journal of Organic Chemistry - The structure of 6-polyfluoroalkyl-2-thiouracils and reactivity of nucleophilic centers in their molecules were analyzed by quantum chemical calculations.... 相似文献
5.
O. G. Khudina Ya. V. Burgart V. I. Saloutin M. A. Kravchenko 《Russian Journal of Organic Chemistry》2011,47(6):904-909
5-Fluoroalkyl-5-hydroxy-4-hydroxyimino-1-isonicotinoyl-4,5-dihydro-1H-pyrazoles were synthesized via a one-pot procedure from polyfluoroalkyl-containing 1,3-diketones, sodium nitrite in acetic
acid, and isoniazid. Acetylacetone gave rise to 3-hydroxyiminopentane-2,4-dione monoisonicotinoylhydrazone which underwent
intramolecular cyclization to 5-hydroxy-4-hydroxyimino-1-isonicotinoyl-3,5-dimethyl-4,5-dihydro-1H-pyrazole on heating in ethanol. The synthesized compounds exhibited moderate tuberculostatic activity. 相似文献
6.
Ivanova A. E. Khudina O. G. Burgart Ya. V. Pervova M. G. Ezhikova M. A. Kodess M. I. Ulitko M. V. Saloutin V. I. 《Russian Chemical Bulletin》2019,68(6):1190-1195
Russian Chemical Bulletin - The alkylation of 6-(polyfluoro)alkyl-2-thiouracils with 4-bromobutyl acetate in refluxing acetonitrile in the presence of K2CO3 proceeds regioselectively to give S,... 相似文献
7.
Acyclic N,N′-(poly)ethylene-bis(2-arylazo-1,3-aminovinylketones) are the main products in the reactions of fluoroalkyl-containing 2-arylhydrazono-1,3-diketones with ethylenediamine, diethylenetriamine and triethylenetetramine. Nickel(II) and copper(II) chelates were obtained from N,N′-ethylene-bis(2-arylazo-1,3-aminovinylketones). 2-Arylhydrazono-3-fluoroacyl esters formed N,N′-ethylenediamides of 2-arylhydrazono-3-fluoroacylpropionic acids with ethylenediamine. Interaction of 2-arylhydrazono-3-fluoroacyl esters with diethylenetriamine and triethylenetetramine resulted in and decomposition products. 相似文献
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9.
Ivanova A. E. Khudina O. G. Burgart Ya. V. Saloutin V. I. 《Russian Chemical Bulletin》2011,60(5):937-941
3-Polyfluoroalkyl-1,2-dihydroquinoxalin-2-ones react with 4-bromobutyl acetate to furnish 1-(4-acetoxybutyl)quinoxalin-2-ones
and 2-(4-acetoxybutoxy)quinoxalines in the ratio 2: 1. Deacylation of these compounds under acidic conditions gives the corresponding
1-(4-hydroxybutyl)- and 2-(4-hydroxybutoxy)-substituted quinoxalines. The structures of compounds synthesized were established
by X-ray crystallography, IR spectroscopy, 1H and 19F NMR spectroscopy, GLC-MS. 相似文献
10.