Victor I. Saloutin

From oxides of internal perfluoroolefins to fluorocontaining camphor thiazolinylhydrazones

Abstract The reaction of oxides of internal trans - and cis -perfluoroolefins with ( 1S , 4S )- or racemic camphor thiosemicarbazone leads to the formation of trans - and cis -isomers of ( 1S , 4S )- or racemic camphor 5′-fluoro-4′-hydroxy-4′,5′-di(perfluoroalkyl)-1′,3′-thiazolinyl-2′-hydrazones, respectively. Unsymmetrical dodecafluoro-2,3-epoxyhexane yields a mixture of regioisomeric hydrazones. The molecular structure of the trans -isomer of ( 1S , 4S )-camphor 5′-fluoro-4′-hydroxy-4′,5′-bis(trifluoromethyl)-1′,3′-thiazolinyl-2′-hydrazone has been established by X-ray crystallography. The quite rare example of cocrystallization of two diastereomers of the latter in homochiral crystal (sp. group P2 1 ) has been revealed.

Alkyl 2-arylhydrazinylidene-3-oxo-3-polyfluoroalkylpropionates as new effective and selective inhibitors of carboxylesterase.

A series of alkyl 2-Arylhydrazinylidene-3-oxo-3-polyfluoroalkylpropionates was synthesized and their inhibitory activity with respect to porcine liver carboxylesterase (CaE, EC 3.1.1.1), human erythrocyte acetylcholinesterase (AChE, EC 3.1.1.7), and horse serum butyrylcholinesterase (BChE, EC 3.1.1.8) was studied. The molecular docking method was used to study the binding mode of the compounds in the active site of CaE. It was found that compounds containing the trifluoromethyl group in the third position of carbonyl chain are highly effective and selective inhibitors of CaE with nanomolar IC50 values, which agrees well with the results of molecular docking.

Transformations of 4-Hydroxy-5,6,7,8-tetrafluorocoumarin Derivatives with Monoamines

The 4-hydroxy-5,6,7,8-tetrafluorocoumarin reacts with the monoamines to form salts under the mild conditions or the 4-alkyl(aryl)aminocoumarins on refluxing in o-xylene. The 3-acetyl-4-hydroxy-5,6,7,8-tetrafluorocoumarin reacts with the strong basic amines in the polar solvents to give salts that can be transformed into the 3-alkylaminoethylidene-5,6,7,8-tetrafluorobenzopyran-2,4-diones. The latter can be obtained by reaction of the 3-acetylcoumarin with different amines. The reactions of the 3-acetylcoumarin with the strong basic amines in dimethyl sulfoxide lead to the 7-alkylamino-3-alkylaminoethylidene-5,6,8-triflurobenzopyrandiones. The 3-acetimidoyl-4-hydroxy-5,6,7,8-tetrafluoro-coumarin affords the 3-alkylaminoethylidenebenzopyrandiones with the monoamines, but in dimethyl sulfoxide the 7-substituted 3-acetimidoyl-5,6,8-trifluorobenzopyrandiones or the 7-alkylamino-3-alkylaminoethylidene-5,6,8-triflurobenzopyrandiones can be obtained.

RECYCLIZATION OF 7-FLUOROALKYL- 4,7-DIHYDROAZOLO(5,1-c)(1,2,4)TRIAZINES INTO 5-(PYRAZOLINYLHYDRAZONO)AZOLES IN THE REACTIONS WITH HYDRAZIDES AND THIOSEMICARBAZIDE

7-Fluoroalkyl-4,7-dihydroazolo[5,1-c][1,2,4]triazines react with hydrazides and thiosemicarbazide to form 5-(5-hydroxy-5-polyfluoroalkyl-2-pyrazoline-4-ylhydrazono)azoles as a result of triazine ring opening at bond C-7-N-8 and followed by regio-selective condensation.

The electrophilic thionation and chlorination of polyfluorinated α-Keto esters

Abstract The methyl ester of trifluoropyruvic acid reacts with phosphorus pentachloride at the keto carbonyl as well as at the ester carbonyl group. The reaction of polyfluorinated α-keto esters with Davys reagent occurs regioselectively at the keto carbonyl and is accompanied by reduction and thiomethylation.

Synthesis and tuberculostatic activity of functionalized pyrazoles derived from (trifluoromethyl)pyrazole containing a hydrazone group

The condensation of 5-(1-hydrazinylideneethyl)-3-(trifluoromethyl)-1H-pyrazole with trimethyl orthoacetate, dimethylformamide dimethyl acetal, and aryl thioisocyanates resulted in a series of functionalized pyrazoles and their tuberculostatic activity was studied.

A convenient and efficient approach to polyfluorosalicylic acids and their tuberculostatic activity

We have developed the practical method for polyfluorosalicylic acids synthesis via nucleophilic ortho-mono-substitution of fluorine atom with magnesium methoxide. We have managed to increase the yield of targeted polyfluorosalicylic acids from good to quantitative. We have studied the tuberculostatic activity of polyfluorosalicylic acids. It has been found that minimum inhibitory concentration (MIC) of compounds is from 0.7 to 6.5μg/mL depending on the structure.

Novel 3-acetyl-2-methyl-polyfluorochromones in reactions with amines and esters of amino acids

Novel 3-acetyl-2-methyl-polyfluoro-4Н-chromen-4-ones were obtained via one-pot acylation of acetylacetone with polyfluorobenzoyl chlorides. These chromones were shown to form N-substituted 3-amino-1-[2-hydroxy(polyfluoro)phenyl]but-2-en-1-ones in reaction with aliphatic primary amines, esters of amino acids, and aqueous ammonia via opening of the pyrone ring and deacylation.

Polyfluoroalkylated 2-ethoxymethylene- 3-oxo esters: synthesis and chemical properties overview

Abstract The review focuses on the synthesis and chemical properties of polyfluoroalkylated 2-ethoxymethylene-3-oxo esters. The scope and peculiarities of their use as organic reagents in reactions with various N-, C-, O-, mono- and dinucleophiles are discussed in detail. The high reactivity of such derivatives is employed in the construction of enaminoketone, arene and heterocycle frameworks. Particular attention is paid to applications of these building blocks as chemicals for fine organic synthesis, bioactive compounds and metal complexes synthesis.

Novel Reagents for Multi-Component Reactions

Ketenimines are a class of versatile and highly reactive intermediates that can participate in a variety of organic reactions, such as nucleophilic additions, radical additions, [2 + 2] and [2 + 4] cycloadditions, and sigmatropic rearrangements. In this presentation, we report on a series of multi-component reactions that involve a ketenimine intermediate. These reactions could furnish diverse heterocyclic compounds, including functionalized iminocoumarin, iminodihydroqunolines, iminothiochromens, pyrrolines, isoquinolines, pyridines, β-lactams, imino-1,2-dihydrocoumarins, and benzimidazoles.