M. V. Goryaeva

New chiral metal complexes based on 2-ethoxymethylidene-3-oxo-3-polyfluoroalkylpropionates

Ethyl 2-ethoxymethylidene-3-oxo-3-polyfluoroalkylpropionates reacted with (1S,2S)-1,2-diphenylethane-1,2-diamine to give diethyl 2,2′-{[(1S,2S)-diphenylethane-1,2-diyl]bis[iminomethylidene]}bis(3-oxo-3-polyfluoroalkyl)alkanoates which were used as ligands to obtain chiral complexes with transition metals.

Regiodirected synthesis of polyfluoro-alkylated pyrimido[1,2-a]benzimidazoles

Conditions have been found for the regiodirected cyclization of 2-aminobenzimidazoles using ethyl 3-oxo-3-polyfluoroalkyl-2-ethoxymethylidenepropionates at the ethoxymethylidenefluoroacyl fragment to give ethyl pyrimidobenzimidazole-3-carboxylates.

Synthesis of Pyrimido(1,2-a)benzimidazoles from Ethyl 2-Ethoxymethylidene-3-oxo-3-(polyfluoroalkyl)propionates

Cyclization of ethyl 2-ethoxymethylidene-3-oxo-3-polyfluoroalkylpropionates with benzimidazol-2-amine in boiling 1,4-dioxane followed two concurrent pathways with participation of fluoroacyl and ethoxycarbonyl fragments and formation of, respectively, ethyl 4-hydroxy-4-polyfluoroalkyl-1,4-dihydropyrimido-[1,2-a]benzimidazole-3-carboxylates and 3-polyfluoroacylpyrimido[1,2-a]benzimidazol-4-ols. Dihydropyrimido[1,2-a]benzimidazole derivatives undergo dehydration to give ethyl 4-(polyfluoroalkyl)pyrimido[1,2-a]benzimidazole-3-carboxylates, whereas the hydroxy group in 3-polyfluoroacylpyrimido[1,2-a]benzimidazol-4-ols is capable of being replaced by the amino group of the second benzimidazole molecule with formation of 4-(1H-benzimidazol-2-ylamino)-3-polyfluoroacylpyrimido[1,2-a]benzimidazoles.

Reaction of 2-(ethoxymethylidene)-3-oxo carboxylic acid esters with tetrazol-5-amine

Abstract2-(Ethoxymethylidene)-3-oxo carboxylic acid esters reacted with tetrazol-5-amine to give ethyl 4-alkyl-2-azidopyrimidine-5-carboxylates capable of undergoing subsequent nucleophilic substitution of hydrogen on C6 or azido group. The reaction of ethyl 2-benzoyl-3-ethoxyprop-2-enoate with tetrazol-5-amine was accompanied by partial decomposition to afford a mixture of ethyl 3-oxo-3-phenylpropanoate and ethyl 7-(1-ethoxy-1,3-dioxo-3-phenylpropan-2-yl)-5-phenyl-4,7-dihydrotetrazolo[1,5-a]pyrimidine-6-carboxylate. Ethyl 7-hydroxytetrazolo[1,5-a]pyrimidine-6-carboxylate was formed as a result of cyclization of diethyl 2-(ethoxymethylidene)propanedioate with tetrazol-5-amine.

New tetradentate N2O2-ligands based on 2-ethoxymethylidene-3-oxo-3-polyfluoroalkylpropionates and ethylenediamine

Condensation of ethylenediamine at the ethoxymethylidene substituent of ethyl 2-ethoxymethylidene-3-oxo-3-polyfluoroalkylpropionates gave diethyl N,N′-ethylenebis(2-aminomethylidene-3-oxo-3-polyfluoroalkylpropionates) as new tetradentate N2O2-ligands which were used to obtain the corresponding metal complexes.

The novel approaches towards fluoroalkyl-containing heteroannulated pyrimidines

The review is focused on the synthesis of fluoroalkyl-containing heteroannulated pyrimidines via the reactions of alkyl 3-oxo-3-polyfluoroalkylpropionates and their ethoxymethylidene and 2-arylmethylidene derivatives with hetarylamines. Heteroannulation of polyfluoroalkyl-containing pyrimidines is also discussed.