Russian Journal of Organic Chemistry最新文献

The two-step method for the synthesis of previously unknown 1-hydroxy-2,3-dihydropyrazolo[1,2-c]­benzo-1,3,4-thiadiazepin-11(5H)-one has been developed based on 2-mercaptobenzoic acid hydrazide and commercially available formaldehyde and acrolein. The synthesized compound, which has a targeted antitumor effect, is a promising bioactive co-ligand for obtaining gold glyco-nanoparticles for biomedical purposes.

– In a simple and efficient convenient method, a series of new fused heterocycles of [1,3]thiazolo[4,5-d]­pyrimidines, 4a–4c were synthesized with good yields. As starting materials, thiosemicarbazide was condensed with 4-N,N-dimethylbenzaldehyde to afford thiosemicarbazone 1 which further cyclized with mercaptoacetic acid to produce 4-thiazolidinone 2. Furthermore, chalcones 3a–3c was prepared through fusion of 4-thiazolidinones with various aldehydes. Finally, the entitled compounds 4a–4c has been obtained via Michael addition reaction of 4-thiazolidinones with thiourea. The chemical structures for all new compounds were deduced from their elemental and spectral analysis.

The reaction of 5-allenyl-2,3,5-trichlorocyclopentenone with glycine, L-methionine, L-leucine, and L-tyrosine methyl esters gave the corresponding Ad_NE adducts, and the subsequent oxidative cleavage of the allene fragment afforded new 4-carboxymethylidene derivatives.

Mono- and dioctyl-substituted benzo[b]benzo[4,5]thieno[2,3-d]thiophenes C8-BTBT and C8-BTBT-C8 that are widely used as organic semiconductors in the manufacture of various organic electronic devices have been synthesized in two steps, by Friedel–Crafts acylation of benzo[b]benzo[4,5]thieno[2,3-d]­thiophene (BTBT) and subsequent reduction of the ketone group(s). Taking into account that the limiting stage in the synthesis of such compounds is the reduction stage, different methods for the reduction acyl-substituted BTBT derivatives have been studied and probable reduction mechanisms have been proposed. The best results in the keto group reduction stage have been obtained with the use of hydrazine hydrate as reducing agent.

A novel series of pyrrolidinylquinoline–imidazolyl-1,2,3-triazole hybrids were synthesised starting from 2-(pyrrolidine-1-yl)quinoline-3-carbaldehyde. The aldehyde was reacted with o-phenylenediamine to produce benzimidazole derivative which was alkylated with propargyl bromide and then subjected to copper-catalyzed azide–alkyne cycloaddition to afford the desired 1,2,3-triazole derivatives. The cycloaddition step was performed under both traditional stirring and microwave irradiation. All synthesized triazole derivatives were screened for their in vitro antimicrobial activity against various bacterial and fungal pathogens. The majority of the synthesized compounds demonstrated moderate to good inhibition zones compared to the standard drugs.

Modification of 2-acetyl-3H-benzo[f]chromen-3-one and 2-[(2E)-3-phenylprop-2-enoyl]-3H-benzo[f]chromen-3-one has been performed for the first time via the reaction with indole. The resulting benzo­[f]coumarins have been found to exhibit antioxidant properties in model systems: they react with hydrogen peroxide and sodium hypochlorite and regulate redox state of rat C6 glioma cells, which is reflected in reduced concentration of intracellular hydrogen peroxide and increased level of reduced glutathione. The synthesized compounds in the presence of exogenous hydrogen peroxide exert a protective effect on the cells, acting as antioxidants and restoring the redox balance. 2-[3-(1H-Indol-3-yl)-3-phenylpropanoyl]-3H-benzo[f]khromen-3-one at a micromolar concentrations inhibited the rat C6 glioma cell proliferation by 25–35%.

The review summarizes literature data on new nucleophilic functionalization reactions of tropylium salts with heterocyclic amines and monocarboxylic acid amides and hydrazides over the past decade.

The reaction of perfluorotetralin with zinc in DMF, followed by treatment with water, gave 1,1,2,2,3,3,4,4,5,6,8-undecafluorotetralin, perfluoro-2,2′-binaphthalene, and octafluoronaphthalene. Under similar conditions, perfluoro-1-ethyltetralin was converted into a mixture of 1,2,3,4,6,7-hexafluoro-5-(per­fluoro­ethyl)naphthalene and perfluorinated 1-ethyl- and 1-vinylnaphthalenes, perfluoro-6-methyltetralin gave rise to 1,2,4,5,6,8-hexafluoro-3-(trifluoromethyl)naphthalene and perfluoro-2-methylnaphthalene, and per­fluoro-1-methylnaphthalene was obtained from perfluoro-4-methyl-1,2-dihydronaphthalene. Perfluoro-1-ethyl­tetralin reacted with bromine-activated zinc in DMF to produce a mixture containing (perfluoro-4-ethylnaph­thalen-1-yl)zinc bromide which was converted to 1,2,3,4,6,7-hexafluoro-5-(perfluoroethyl)naphthalene by the action of water, while its reaction with CuCl₂ afforded perfluoro-4,4′-diethyl-1,1′-binaphthalene.

The reaction of ethyl pyridine-2-ylcarbamate with phenacyl bromides in acetonitrile gave 2-aryl-1-(ethoxycarbonyl)-2-hydroxy-2-phenyl-2,3-dihydro-1H-imidazo[1,2-a]pyridine-4-ium bromides which were con­­verted into 2-arylimidazo[1,2-a]pyridines by heating in acetic anhydride, followed by treatment with potassium carbonate.

Unusual direction of the C–H arylation of 2-(het)aryl[1,2,4]triazolo[1,5-a]pyrimidines with (het)aryl halides under catalysis by ruthenium(II) complexes has been revealed. The reaction involved activation of the C⁷–H bond rather than the C^α–H bond of the (het)aryl substituent at C² of the triazolopyrimidine core. The arylation of 2-substituted [1,2,4]triazolo[1,5-a]pyrimidines with (het)aryl bromides afforded a series of 7-(het)aryl derivatives in good yields.