E. S. Meshcheryakova

Efficient catalytic synthesis of (1,5,3-dithiazepan-3-yl)quinolines

Abstract(1,5,3-Dithiazepan-3-yl)quinolines were obtained in high yields by the reaction of 1-oxa-3,6-dithiacycloheptane with quinolinamines in the presence of a catalyst Sm(NO3)3·6H2O.

Synthesis of N-Hydroxyalkyl-1,5,3-Dithiazepanes Based on Amino Alcohols

Catalytic methods were developed for the synthesis of N-hydroxyalkyl-1,5,3-dithiazepanes by recyclization of 1-oxa-3,6-dithiacycloheptane with amino alcohols and by intermolecular cyclization of 1,2-ethanedithiol with methoxymethylamino alcohols.

Catalytic cycloaminomethylation of ureas and thioureas with N,N-bis(methoxymethyl)alkanamines

An efficient procedure has been developed for the synthesis of 5-alkyl-1,3,5-triazinan-2-ones, 5-alkyl-1,3,5-triazinane-2-thiones, and 2,6-dialkylhexahydro-2,3a,4a,6,7a,8a-hexaazacyclopenta[def]fluorene-4,8(1H,5H)-diones by reactions of urea, thiourea, and tetrahydroimidazo[4,5-d]imidazole-2,5-(1H,3H)-dione with N,N-bis(methoxymethyl)alkanamines in the presence of SmCl3 · 6 H2O as catalyst.

Synthesis of bis-1,5,3-dithiazepanes on the basis of aromatic diamines

A procedure has been developed for the synthesis of N,N′-disubstituted bis-1,5,3-dithiazepanes by samarium-catalyzed recyclization of 1,3,6-oxadithiepane with aromatic diamines.

Efficient synthesis of cyclophanes containing sulfur and nitrogen atoms by cycloaminomethylation of benzenedithiols in the presence of samarium-based catalysts

An efficient procedure has been developed for the synthesis of 3-aryl-3,4-dihydro-2H-1,5,3-benzodithiazepines, 4-aryl-2,6-dithia-4-azabicyclo[5.3.1]undeca-1(11),7,9-trienes, and 4,10,16-triaryl-2,6,8,12,14,18-hexathia-4,10,16-triaza-1,7,13(1,4)-tribenzenacyclooctadecaphanes by samarium-catalyzed cycloaminomethylation of benzenedithiols with N,N-bis(methoxymethyl)anilines.

Synthesis of Dithiaza- and Dioxadithiazacycloalkanes by Cyclothiomethylation of Arylamines with Formaldehyde and α,ω-Dithiols

New derivatives of 1,5,3-dithiazepanes and macroheterocycles were synthesized by a three-component cyclothiomethylation of arylamines with formaldehyde and α,ω-dithiols. The sorption properties of 3-phenyl-1,5,3-dithiazepane and 6-phenyl-1,11-dioxa-4,8-dithia-6-azacyclotridecane applicable for the extraction of Ag(I) and Pd(II) ions from nitric acid solutions at room temperature were studied by a static method.

Haloiminolactonization of cyclopentene α,α-dichlorocarboxamides. Tandem rearrangement of iminolactones in epoxylactones

Electrophilic cyclization initiated by NBS and I2 of 2,2-dichloro-2-[(1R,5S)- and 2,2-dichloro-2-[(1S,5R)-5-hydroxy-2-cyclopent-2-en-1-yl]-N-[(1R)-1-phenylethyl]acetamides was investigated. Stable under conditions of chromatography on SiO2 bicyclic iminoesters, (2Z,3aS,4S,6S,6aS)-6-bromo-3,3-dichloro- and (2Z,3aS,4S,6S,6aS)-3,3-dichloro-6-iodo-2-{[(1R)-1-phenylethyl]imino}hexahydro-2H-cyclopenta[b]furan-4-ols were isolated and characterized, and a possible version was suggested of their step-by-step recyclization transformations. The halocyclization of carboxamides in water-organic mixtures afforded bicyclic epoxylactones (1aR,2aS,5aS,5bS)- and (1aS,2aR,5aR,5bR)-5,5-dichlorohexahydro-4H-oxireno[3,4]cyclopenta-[1,2-b]furan-4-ones, whose reductive dechlorination proceeded stepwise with successive removal of Cl atoms and led to the formation of (1aR,2aS,5aS,5bS)- and (1aS,2aR,5aR,5bR)-hexahydro-4H-oxireno[3,4]cyclopenta-[1,2-b]furan-4-ones.

Structure and Conformational Analysis of 5,5-Bis(bromomethyl)-2-(4-methoxyphenyl)-1,3-dioxane

The structure of 5,5-bis(bromomethyl)-2-(4-methoxyphenyl)-1,3-dioxane has been studied by 1H and 13C NMR and X-ray diffraction. Molecules of the title compound exist in the chair conformation with equatorial orientation of the methoxyphenyl substituent. The dioxane ring inversion path, free conformational energy, and optimal conformation of the aryl group have been determined by computer simulation in terms of the DFT PBE/3ζ method. The calculation results are consistent with the X-ray diffraction data.

Direction of the Reaction of 6-Methylpyrimidine-2,4(1H,3H)-dione with 2-Chloromethylthiirane: N1- or N3-Thietanyl Derivative?

The reaction of 6-methylpyrimidine-2,41H,3H-dione with 2-chloromethylthiirane gave 6-methyl-N-thietan-3-ylpyrimidine-2,41H,3H-dione. Its oxidation subsequent reaction of the resulting N-1,1-dioxo-λ6-thietan-3-yl derivative with ethyl chloroacetate afforded the corresponding ethyl pyrimidinylacetate. The structure of the latter was determined by X-ray analysis, which confirmed the formation of N3-thietan-3-yl derivative rather than its N1-substituted isomer in the title reaction. According to the results of B3LYP/6-31G++d,p, PBE/3ζ, MP2/6-31G++d,p quantum chemical calculations,the N3-thietanyl derivative is more stable than the N1-isomer. It was also found that the calculated barrier to internal rotation of the thietanyl group about the N–C bond in 6-methyl-3-thietan-3-yl-pyrimidine-2,41H,3H-dione is lower than in the N1-isomer.

Atropisomeric N-acyl-N-(cyclopentenylphenyl)glycines in the synthesis of oxazolo[3,4-a]benzoxazocinones

Intramolecular [3+2]-cycloaddition was studied of munchnones generated at heating syn- and anti-atropisomers of N-acyl-N-[6-methyl-2-(cyclopent-2-en-1-yl)phenyl]glycines with acetic anhydride. By spectral and X-ray diffraction analysis syn-isomers of acids and tetrahydro-1,4,7-methanetriyl[1,3]oxazolo[3,4-a][1]- bensazocin-3(3aH)-ones were identified.