T. V. Rybalova

Reaction of Arylpropargyl Aldehydes with 2,3-Bis-hydroxylamino-2,3-dimethylbutane: Synthesis of 2-(1-Hydroxy-4,4,5,5-tetramethylimidazolidin-2-ylidene)-1-arylethanones

Abstract Reaction of arylpropargyl aldehydes with 2,3-dihydroxylamino-2,3-dimethylbutane results in the formation of 2-(1-hydroxy-4,4,5,5-tetramethylimidazolidin-2-ylidene)-1-arylethanones in high yields (70–80%). Allowing availability of propargyl aldehydes, this method gives new possibilities for the preparation of 2-(1-hydroxy-4,4,5,5-tetramethylimidazolidin-2-ylidene)-1-arylethanones.

SYNTHESIS AND STUDY OF MUTAGENIC PROPERTIES OF LUPANE TRITERPENOIDS CONTAINING 1,2,3-TRIAZOLE FRAGMENTS IN THE C-30 POSITION

New derivatives of betulin, betulinic acid methyl ester, and their acetate analogs containing 1,2,3-triazole fragments in the C-30 position were synthesized. It was shown using the Ames test that 30-azidolup-20(29)-enes and 3β,28-diacetoxy-30-(4-R-1,2,3-triazol-1-yl)lup-20(29)-enes did not exhibit mutagenic properties.

Reactions of N,N-(dialkyl)arylthioacetamides with dialkyl acetylenedicarboxylates

Abstract2-(Alkoxycarbonylmethylidene)-4-aryl-5-(dialkylamino)thiophen-3(2H)-ones were synthesized by condensation of N,N-(dialkyl)arylthioacetamides with dialkyl acetylenedicarboxylates. Intermediate substituted vinylic sulfides were isolated. When heated or in the presence of an acid or a base, they undergo cyclization into thiophenes.

Synthesis of (7-polyfluoroalkyl)pyrazolo[1,5-a]pyrimidines based on lithium fluorine-containing β-diketonates

The reactions of Li enolates of fluorine-containing β-diketones with 3-aminopyrazoles afforded (7-polyfluoroalkyl)pyrazolo[1,5-a]pyrimidines. The structure of 3-bromo-2-methyl-5-phenyl-7-trifluoromethylpyrazolo[1,5-a]pyrimidine was established by X-ray diffraction analysis.

Synthetic transformations of sesquiterpene lactones: VII. Palladium-catalyzed cross-coupling of isoalantolactone with 5-halouracils

Palladium-catalyzed cross-coupling of isoalantolactone with 1,3-disubstituted or 1-substituted 5-bromo(iodo)uracils afforded mainly (13E)-13-(2,4-dioxotetrahydropyrimidin-5-yl)eudesma-4(15),11(13)-dien-8β,12-olides whose yields depended on the composition of the catalytic system, base, and additive. The structure of (13E)-13-[3-(2-cyanoethyl)-2,4-dioxotetrahydropyrimidin-5-yl]eudesma-4(15),11(13)-dien-8β,12-olide was proved by X-ray analysis.

Amination of 5-hydroxy-1,4-naphthoquinone in the presence of copper acetate

The reaction of 5-hydroxy-1,4-naphthoquinone with butylamine in the presence of copper(II) acetate monohydrate on heating resulted in the formation of a mixture of regioisomeric 2,6- and 2,8-bis(butylamino)-5-hydroxy-1,4-naphthoquinones.

Reactions of perfluorinated 1-ethyltetrahydronaphthalene, 1-ethylindan, and 1,1-diethylindan with pentafluorobenzene in antimony pentafluoride

The reaction of perfluoro(1-ethyltetrahydronaphthalene) with pentafluorobenzene in SbF5, followed by treatment of the reaction mixture with water, afforded a mixture of 1-hydroxyperfluoro(1-phenyl-4-ethyletetrahydronaphthalene) and perfluoro(5-phenyl-8-ethyl-2,6,7,8-tetrahydronaphthalen-2-one). From perfluoro(1,1-diethylindan), 1-hydroxyperfluoro(1,1-diethyl-3-phenylindan) was obtained. Perfluoro(1-ethylindan) reacted with an equimolar amount of pentafluorobenzene in SbF5 to give (after hydrolysis) 1-hydroxyperfluoro-(3-ethyl-1-phenylindan), 1-hydroxyperfluoro(3-ethyl-1,3-diphenylindan), and perfluoro(1-ethyl-1-phenylindan), while in the reaction with excess pentafluorobenzene, followed by treatment with anhydrous hydrogen fluoride, perfluoro(1-ethyl-3-phenylindan) and perfluoro(1-ethyl-1,3-diphenylindan) were formed.

Synthesis and molecular and crystalline structure of polyfluoro-1,3-diazafluorenes

Reactions of 2-amino-3-(1-imino-2,2,2-trifluoroethyl)hexafluoro-1H-indene with carboxylic acid anhydrides and chlorides afforded 2-alkyl(aryl)-4-trifluoromethyl-5,6,7,8,9,9-hexafluoro-1,3-diazafluorenes. The molecular and crystalline structure of the products was studied by NMR spectroscopy and X-ray diffraction. 5,6,7,8,9,9-Hexafluoro-2-phenyl-4-trifluoromethyl-1,3-diazafluorene in crystal gives rise to infinite ladder chains via π-stacking interaction between the benzene ring of one molecule and tetrafluorobenzene fragment of the other.

Triterpenoids from species ofAbies hill. II. Abiesolidic acid — A new 3,4-secolanostanoid from the oleoresin ofAbies sibirica

The oleoresin of the Siberian fir has yielded a new 3,4-secolanostanoid for which the structure of (20R,23S,25R)-3,4-seco-9β-lanosta-4(28),7-dien-26,23-olid-3-oic acid has been established by x-ray structural analysis. The pathways of the mass-spectrometric fragmentation of this acid and its esters have been investigated.

Synthetic transformations of sesquiterpene lactones. V.* Synthesis and cytotoxicity of 13-aryl-substituted tourneforin derivatives

13-Aryl-substituted tourneforin derivatives were synthesized via the Heck reaction with aryliodides. The structure of (E)-13-(3,4-dimethoxybenzyl)-eudesma-4(5),11(13)-dien-6α,12-olide was confirmed by an XSA. A study of the cytotoxicity of the synthesized derivatives for CEM-13, MT-4, and U-937 tumor models showed promise for the modification.