N. D. Chkanikov

Reaction of 1,1-dicyano-2,2-bis(trifluoromethyl)ethylene with arylamines

Abstract We have studied the nature and determined the application boundaries of C-alkylation of various arylamines and their derivatives with 1,1-dicyano-2,2-bis(trifluoromethyl)ethylene. The possibility of formation in these reactions of heterocyclic vicinal enaminonitriles has been shown. It has been found that in certain cases the reactions owe their complexity to oxidation- reduction process in which the electrophilic alkene plays the role of dehydrogenation agent.

Reactions of highly electrophilic polyfluoro unsaturated compounds with pyrazole derivatives

Pyrazole derivatives were hydroxyalkylated at the C4 atom by hexafluoroacetate and methyl trifluoropyruvate. The products of the hydroxyalkylation were dehydrated to the corresponding alkylidene derivatives which were reacted with nucleophiles. Dicyanoethylenes, obtained from polyfluorocarbonyl compounds, alkylated pyrazol-5-ones with the formation of pyrazolopyran derivatives.

Heterocyclization of 1,1-dicyano-2-(trifluoromethyl)ethylenes with 1,3,3-trimethyl-3,4-dihydroisoquinoline and its derivatives

Abstract1,3,3-Trimethyl-3,4-dihydroisoquinolines react with 1,1-dicyano-2,2-bis(trifluoromethyl)ethylene to give 4-amino-6,6-dimethyl-2,2-bis(trifluoromethyl)-3-cyano-6,7-dihydro-2H-benzo[a]quinolizines. The reaction of 3,3-dimethyl-1-cyanomethylidene-1,2,3,4-tetrahydroisoquinoline and the methyl ester of 3,3-dicyano-2-(trifluoromethyl)acrylic acid leads to 5,5-dimethyl-3-oxo-2-(trifluoromethyl)-2-(dicyanomethyl)-2,3,5,6-tetrahydropyrrolo[2,1-a]isoquinoline.

Heterocyclization reactions of CF3-substituted 1,1-dicyanoethylenes with nitrogen-containing compounds

Abstract The reactions of 1,1-dicyano-2,2-bis(trifluoromethyl)ethylene and esters of 3,3-dicyano-2-(trifluoromethyl)acrylic acid with aryl amines, nitrogen-containing heterocycles and enamines were studied. The possibility of heterocyclic vicinal enaminonitrile formation in these reactions was shown. In certain cases, reactions with the participation of (trifluoromethyl)acrylic acid derivatives lead to lactams. A novel reaction of 1,1-dicyano-2-(trifluoromethyl) ethylenes with aryl amines in the presence of carbonyl compounds leading to the trifluoromethyl substituted derivatives of 1-aryl-l,4-dihydropyridine was investigated.

Hexafluoroacetone and methyl trifluoropyruvate as precursors of modified esters of N-acyl-N-phenyl-?-amino acids

The C-oxyalkylation of N-aryl-α-amino acids by hexafluoroacetone (1) and methyl trifluoropyruvate (2), followed by acylation of the products3–13, 15, and17 formed, was carried out. The activity of the synthesized anilides against pathogens of plant fungus diseases was studied.

C-ALKYLATION OF INDOLES BY 1,1-BIS(TRIFLUOROMETHYL)-2,2-DI-CYANOETHYLENE AND 2-TRIFLUOROMETHYL-3,3-DICYANOACRYLIC ACID ESTERS

Indole and its derivatives with various substituants in the 1 and 2 positions of the indole ring react with 1,1-bis(trifluoromethyl)-2,2-dicyanoethylene and 2-trifluoromethyl-3,3-dicyanoacrylic acid esters to give C3-alkylation products.

Reactions of diarylamines with hexafluoroacetone

Diphenylamine reacts with hexafluoroacetone to give a mixture of products, of which 2-(1-hydroxy-1-trifluoromethyl-2,2,2-trifluoroethyl)diphenylamine (II) was isolated. N-Arylanthranilic acids modify the 1,1,1,3,3,3-hexafluoro-2-hydroxy-2-propyl group upon the reaction of its sodium salt with the hydrate of hexafluoroacetone (I) under mild conditions. This method gave 4-(1-hydroxy-1-trifluoromethyl-2,2,3-trifluoroethyl)-N-(2,3-xylyl)anthranilic acid from N-(2,3-xylyl)anthranilic acid in 93% yield.

Reactions of 1,1-dicyano-2-bis-(trifluoromethyl)-ethylens with enamines

Abstract A novel reaction of 1,1-dicyano-2-bis (trifluoromethyl) ethylenes (I) with aryl amines in the presence of carbonyl compounds leading to the trifluoromethyl substituted derivatives of 1,4-dihydropyridine is found and investigated. The cyclization reactions ( I ) with classic enamines are also studied.