Andrew M. Moiseev

A novel method for the oxidation of thiophenes. Synthesis of thiophene 1,1-dioxides containing electron-withdrawing substituents

A novel method for the synthesis of thiophene 1,1-dioxides by oxidation of substituted thiophenes with trifluoroperoxyacetic acid was developed. The effect of the solvent nature on the course of the reaction was studied and optimum conditions for the oxidation of thiophenes containing various functional groups were found. Previously unknown thiophene dioxides were obtained.

Reactions of acceptor thiophene 1,1-dioxides with dienes. Synthesis of bisadducts

Cycloaddition of dienes to thiophene dioxides affords mono-and bisadducts, depending on the reaction conditions. Regio-and stereochemical specific features of the cycloaddition were revealed. The thermal rearrangement of the monoadduct was found.

Reaction of 2-Aminothiazoles and Their Benzo- and Naphtho Derivatives with β-Sulfonyltrifluoromethylvinyldiols

By cyclocondensation of 2-aminothiazoles and their benzo and naphtho analogs with β-sulfonyltrifluoromethylvinyldiols, we have obtained a series of novel CF3-containing 6,7-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidines. In the case of the sterically hindered 2-aminothiazoles, heterocyclization does not occur and the corresponding enamino ketones are formed.

Reactions of electron-withdrawing thiophene 1,1-dioxides with furans. A novel reaction pathway

Reactions of thiophene dioxides containing electron-withdrawing substituents with furans were studied. The reactions with unsubstituted furan followed the inverse-electron-demand Diels-Alder mechanism. Subsequent elimination of sulfur dioxide from the adduct afforded products of the tetrahydrobenzofuran series. The reactions with substituted furans gave benzylcarbonyl compounds in high yields. The observed regiochemistry of the reaction was explained in terms of the frontier orbital theory using the calculated orbital coefficients.

Cyclocondensation of 2-Amino-1,3,4-thiadiazoles with β-Sulfonylvinyltrifluoromethyldiols

A series of CF3-containing 6,7-dihydro-5H-[1,3,4]thiadiazolo[3,2-a]pyrimidin-7-ols was obtained by the interaction of 2-amino-1,3,4-thiadiazoles with β-sulfonylvinyltrifluoromethyldiols and their stereochemistry was established. The structure of 5-(phenylsulfonyl)-7-(trifluoromethyl)-6,7-dihydro-5H-[1,3,4]thiadiazolo[3,2-a]pyrimidin-7-ol was confirmed by X-ray crystallography.