V. I. Filyakova

Aminovinyl ketones and aminovinyl esters as CCN building blocks for the synthesis of 1H-pyrrolo[3,2-e]1,2,4-triazines

5,6-Unsubstituted-3-aryl-1,2,4-triazines were found to react with aminovinyl ketones and aminovinyl esters in acetic anhydride to form derivatives of 3a,4,7,7a-tetrahydro-1H-pyrrolo[3,2-e]1,2,4-triazines in good yields.

Fluoroalkyl-containing lithium β-diketonates in the synthesis of 1,2,4-triazolo[1,5-a]pyrimidines

Cyclocondensation of fluorine-containing lithium β-diketonates with 3-amino-1,2,4-triazoles afforded 7-fluoromethyl-1,2,4-triazolo[1,5-a]pyrimidines.

Synthesis, structure, electrochemical and magnetic properties of 2,6-bis(5-trifluoromethylpyrazol-3-yl)pyridine and its NiII complexes

Abstract2,6-Bis(5-trifluoromethylpyrazol-3-yl)pyridine (H2L) and its mono-, tri-, and tetranuclear NiII complexes were synthesized for the first time. All the obtained compounds were characterized by single-crystal X-ray diffraction analysis. In the complexes, 2,6-bis(5-trifluoromethylpyrazol-3-yl)pyridine exists in the neutral and dianionic forms and exhibits different coordination modes (κ3-, μ2-κ3:κ1-, and μ3-κ3:κ1:κ1). The electrochemical and magnetic properties of all compounds were studied. The tetranuclear NiII complex with the L2− dianion is reduced in two sequential reversible one-electron steps.

Synthesis of (7-polyfluoroalkyl)pyrazolo[1,5-a]pyrimidines based on lithium fluorine-containing β-diketonates

The reactions of Li enolates of fluorine-containing β-diketones with 3-aminopyrazoles afforded (7-polyfluoroalkyl)pyrazolo[1,5-a]pyrimidines. The structure of 3-bromo-2-methyl-5-phenyl-7-trifluoromethylpyrazolo[1,5-a]pyrimidine was established by X-ray diffraction analysis.

Synthesis of 3-fluoroalkyl-2-aziridinyl ketones

Simple and efficient methods for the synthesis oftrans-3-fluoroalkyl-2-aziridinyl ketones from polyfluorinated α,β-enones have been developed.

Mono- and diadducts and bicyclic adducts in reactions of 2,3-dicyano-1-ethylpyrazinium cation with C- and O-nucleophiles

Products of diaddition of O- and C-nucleophiles to the 2,3-dicyano-1-ethylpyrazinium cation were isolated for the first time. The tandem AN—AN reactions of 2,3-dicyano-1-ethylpyrazinium tetrafluoroborate with 1,3-diketone enolates or keto esters afforded tetrahydrofuro[2,3-b]pyrazine derivatives, whereas cyclization with ethylene glycol gave tetrahydro-1,4-dioxino[2,3-b]pyrazine. Crystallographic data on the three-dimensional structures of these compounds were reported.

Interaction of fluoroalkyl-containing β-diketones with amines

The composition of products of the interaction of asymmetric fluoroalkyl-containing β-diketones with amines was studied. Mixtures of regioisomeric β-aminovinylketones and products of cleavage and secondary condensation are formed, depending on the temperature, the solvent, the nature of the fluorinated and nonfluorinated substituents in the β-diketone, and the basicity of the amine. The major product is a β-aminovinylketone in which the NH2 group is removed from the fluoroalkyl substituent. No β-aminovinylimines, products of condensation involving two electrophilic centers, were observed.

Chelates of Fluoroalkyl Containing Enaminoketones

The structure and areas of practical application of fluoroalkyl containing enaminoketone chelates with d-metals are reviewed. Synthesis of ligands and the routes to the regioisomeric enaminoketones are also considered.

Annelation of the thiazole ring to 1,2,4-triazines by tandem AN-AN or SNH-SNH reactions

The reactions of 3-aryl-1,2,4-triazines with aromatic thioamides and 4-arylthiosemicarbazides in acetic anhydride at room temperature afforded cyclic products of the tandem nucleophilic addition reactions, viz., tetrahydrothiazolo[4,5-e]-annelated 1,2,4-triazines, in good yields. The latter underwent aromatization in the presence of potassium permanganate.

Fluoroalkyl-substituted lithium 1,3-diketonates in reactions with hetarylhydrazines

Fluoroalkyl-substituted lithium 1,3-diketonates reacted with 4-hydrazinyl-6-methylpyrimidin-2-amine, 2,6-dimethylpyrimidin-4-ylhydrazine, 7-fluoroquinoxalin-6-ylhydrazine, and benzothiazol-2-ylhydrazine to give the corresponding hetaryl-substituted pyrazoles. The molecular and crystal structures of 4-methyl-6-(3-methyl-5-trifluoromethyl-1H-pyrazol-1-yl)pyrimidin-2-amine and 4-(5-difluoromethyl-4,5,6,7-tetrahydro-2H-indazol-2-yl)-6-methylpyrimidin-2-amine were determined by X-ray analysis.