Žurnal organičeskoj himii

Interaction of perfluorobenzocyclobutene with two equivalents of 1,3,5-trifluorobenzene in an SbF₅ medium followed by the treatment of the reaction mixture with water gave (3,4,5,6-tetrafluorobenzene-1,2-diyl)bis[(2,4,6-trifluorophenyl)methanone], 1-(2,4,6-trifluorophenyl)perfluorobenzocyclobuten-1-ol and 4,5,6,7-tetrafluoro-1,3,3-tris(2,4,6-trifluorophenyl)-1,3-dihydro-2-benzofuran-1-ol. When the reaction mixture was treated with HF, 1,2-bis(2,4,6-trifluorophenyl)-perfluorobenzocyclobutene along with 1-(2,4,6-trifluorophenyl)perfluorobenzocyclobutene were obtained. The latter compound reacted with pentafluoro-, 1,2,3,4- or 1,2,4,5-tetrafluorobenzenes in an SbF₅ medium to give corresponding polyfluoro-1,2-diphenylbenzocyclobutenes after treatment of the reaction mixture with HF.

The synthesis of the exo-methylidenecyclopentenone amide given in the title of the article from the methyl ester 2-{(1R,2R,5R)-2-[((tert-butyl(dimethyl)silyloxymethyl]-5-(trimethylsilyl)cyclopent-3-en-1-yl}acetic acid.

Double alkylation reactions of aromatic hydrocarbons with carboxylic acids and hydroxy-substituted mono- and dicarboxylic acids in acidic media have been carried out. The obtained polycarboxylic diadamantylated arenes can be considered as a new type of structurally rigid polycarboxylate ligands in the directed design of metal-organic coordination frameworks.

In continuation of the studies on synthetic modifications of fusidane triterpenoids, an O-propargyl fragment was introduced at the C³ atom of the fusidic acid methyl ester molecule and chemical transformations of the triple bond were carried out through reactions catalyzed by copper(I) salts to obtain an aminomethylene analogue, 1,2,3-triazole, and an aryl-substituted acetylene derivative.

The diverse biological activity of heterocyclic compounds makes them one of the most important areas of pharmaceuticals and organic synthesis. In this work, a synthesis of new hetarylquinolines containing thiazolidine and dihydrothiazole rings was carried out on the basis of 2-{1-[2-methyl-4-(methylthio)-quinolin-3-yl]propan-2-ylidene}hydrazinocarbothioamides substituted in the benzene ring. The synthesis was conducted using readily available and non-toxic starting materials, ensuring a practical and accessible methodology. The results of this work may serve as a foundation for further studies aimed at exploring the biological and applied potential of these compounds.

The conformational preference of oxybis(methylene-1,3-dioxane-5,5-diyl)dimethanol in various solvents was studied by NMR. According to the data of two-dimensional spectroscopy (NOESY), the bis(chair) form with diaxial oxymethyl groups is dominated in С₆D₆ and CDCl₃, while the form with axial and equatorial oxymethyl groups at С⁵ and С^5' atoms of the ring is dominated in DMSO-d₆ and CD₃CN solvents. The results of computer simulation of the conformational transformation of molecules of the studied diformal within the DFT approximation PBE/def2-SVP in these solvents (cluster model) are in complete agreement with the NMR results. It is shown that the optimal number of solvent molecules in the nearest solvate shell of the studied diformal varies from five to seven depending on the nature of solvent.

The interaction of 1-antipyryl-4-aroyl-5-methoxycarbonyl-1H-pyrrole-2,3-diones with dimedone (5,5-dimethylcyclohexanedione-1,3) leads to the formation of 1'-antipyryl-3'-aroyl-4' -hydroxy-6,6-dimethyl-6,7-dihydro-spiro[benzofuran-3,2'-pyrrole]-2,4,5'(1'H, 5H)-triones. Synthesized compounds of interest for pharmacology and medicinal chemistry.

On the basis of helidamic acid, 4-chloropyridine-2,6-dicarboxamide and 4-chloropyridine-2,6-dicarbonitrile were synthesized sequentially, the interaction of which with diethyl acetal aminoacetaldehyde led to 2,6-bis(1H-imidazole-2-yl)-4-chloropyridine, a tridentate ligand.