Chemistry of Heterocyclic Compounds最新文献

The data on multicomponent methods of tetrahydro-4H-indol-4-one synthesis published over the past ten years are summarized in this review. Three main synthetic approaches in the construction of such molecules are considered. Among them are: condensation of cyclohexane-1,3-diones with α-halogenoketones and primary amines, three-component reaction of cyclic enaminoketones, arylglyoxals, and methylene active compounds, and condensation of cyclic enaminoketones and arylglyoxals in the presence of nucleophilic reagents (often solvents). The latter domino reaction runs under microwave irradiation and leads to the functionalization of position 7 of the indole ring system. The material is systematized according to the structure of the starting compounds.

The reactions of nitrosoalkenes, generated in situ from the corresponding α-bromooxime upon the action of a base, with electron-rich olefins were used to synthesize a series of heterocyclic compounds containing 1,2-oxazines, the expected Diels–Alder cycloadducts. The structural features of the obtained heterocyclic compounds were determined based on NMR spectra, HRMS, and X-ray structural analysis.

A new synthetic method to obtain functionally substituted 1,4,2-dioxazoles from vinyl aryl ethers and hydroxamic acids was proposed. The target heterocycles were formed under mild conditions in good yields. It was shown that ring closure occurs via the formation of aroxy(methyl) arylhydroxamates as intermediates.

A one-pot synthesis approach to access sulfonamide-containing derivatives of dibenzo[1,4]thiazepine using primary amines and 2-[(2-nitro-4-sulfamoylphenyl)sulfanyl]benzoic acid as precursors was developed. The approach is based on a sequence of amidation steps and the subsequent tandem of the Smiles rearrangement and denitrocyclization reaction. The resulting tricyclic systems showed pronounced activity as inhibitors of bovine carbonic anhydrase isoform II.

Much synthetic effort is being devoted to the synthesis of fused nitrogen-containing heterocycles. Among them, pyrrolo[1,2-a]quinoline derivatives continue to gain attention from the synthetic community for decades owing to their diverse biological activities and useful functional properties. Recent advances in the preparation of these prominent heterocycles are summarized in this review.

This microreview summarizes the data published over the past 10 years on the methods of synthesis and practical application of tellurium-substituted azoles. The material is systematized by the methods of the C- and N-functionalization of azoles with the construction of the tellurium-containing fragment directly on the azole nucleus or via spacers.

The reactivity of 2,4-diphenylfuran has been studied and its promising potential as a substrate for oxidative homocoupling, lithiation followed by modification, bromination, and subsequent cross-coupling reactions has been demonstrated.

Various furanic conjugated enones, 4-(furan-2-yl)but-3-en-2-ones and 1-aryl-3-(furan-2-yl)prop-2-en-1-ones, have been synthesized from furfural, 5-hydroxymethylfurfural, and its derivatives by aldol condensation. It has been found for the first time, that reactions of these furanic conjugated enones with arenes under the action of triflic acid or AlCl3 afford the corresponding products of hydroarylation of the furan side chain carbon–carbon double bond in 29–89% yields. According to NMR study and DFT calculations, the corresponding O,C-diprotonated species of furanic enones are the reactive electrophilic intermediates. The obtained furan derivatives demonstrate moderate antimicrobial activity against yeast-like fungi Candida albicans at 64 μg/ml concentration. They also suppress Escherichia coli and Staphylococcus aureus.

Recent investigations of intramolecular C–H bond amination reaction of sulfamate ester derivatives forming 1,2,3-oxathiazine-2,2-diones and 5,6-dihydro-1,2,3-oxathiazinane-2,2-diones from 2017 to 2021 are summarized.

In this microreview, articles on the methods of isoxazolidine derivative synthesis published since 2020 are summarized. The methods include non-catalyzed cycloaddition processes, intramolecular cycloaddition reactions, and catalyzed cycloaddition reactions.