Chemistry of Heterocyclic Compounds最新文献

This microreview summarizes the data on the synthesis of salts of five-membered N-heterocyclic compounds published since 2017. The material is systematized on the basis of the number of nitrogen atoms in the five-membered ring.

The development of innovative methods for the construction of heterocycles is an important topic in synthetic and medicinal chemistry. Ring expansion strategies, involving the cyclization of strained aza rings, have been well developed in the synthesis of diverse heterocyclic compounds. This microreview summarizes recent advances in the ring expansion reactions of aziridines, oxetanes, and azetidines to access a series of functionalized 2-oxazolines, which are versatile structural motifs in drugs and bioactive molecules.

New C–N-bonded bisazoles were obtained by cine-substitution of 1,3-dinitro-1H-pyrazole-4-carbonitrile by the action of N-azoles. Their spectral characteristics were investigated using multinuclear NMR spectroscopy.

The method for the preparation of 3,6-disubstituted 1,2,4-triazines based on condensation reaction between easily available α-imino esters and isonitrosoacetophenone hydrazones was reported. The significant differences in reaction conditions, ratio of products, and yields between the developed method and the earlier reported approach were demonstrated. The corresponding 2,5-disubstituted pyridines were synthesized from the prepared 1,2,4-triazines, and their photophysical properties were studied. Studies of the photo-physical properties revealed low and moderate luminescence quantum yields, and negligible solvatochromic behavior in case of 4-methoxyphenylpyridine derivative due to the role of donating methoxy group, however, with a low linearity of a Lippert–Mataga plot. Nevertheless, 2,5-disubstituted pyridines are of interest due to simple protocols of synthesis, moderate photophysical properties, and potential applicability in different scientific and industrial areas.

Minireview describes recent (2014–2024) advances in the synthesis of five- to seven-membered azaheterocycles using heteroannulation of monosubstituted ferrocenes. Most of the methods described here are based on asymmetric transition metal catalysis.

A method for the synthesis of 1,4-dihydroquinoline-3-carbonyl compounds from 2-benzoyl-3-[2-(dialkylamino)aryl]acrylates via the sequence of 1,5-hydride shift, dealkylation, and cyclization processes was proposed. The reaction products contained a push-pull enamine fragment.

The reactions of purine nucleic base perchlorates with the simplest 1,3-diketone – acetylacetone – were studied for the first time. It was demonstrated that adenine reacts with acetylacetone in a 1:2 molar ratio via opening of the pyrimidine fragment of the bicyclic struc- ture, elimination of a one-carbon fragment in the form of a formic acid molecule, and recyclization into 8-(4,6-dimethylpyrimidin-2-yl)- 2,4-dimethylimidazo[1,5-a]pyrimidine. Guanine, in turn, reacted with acetylacetone in a 1:1 ratio and formed 7,9-dimethyl-3H-pyrimido- [2,1-b]purin-10-ium-4-olate. In this case, the direction of heterocyclization differed from that observed in the reaction of guanine with malondialdehyde during the in vitro and in vivo formation of the minor nucleotide base M₁G. The synthesized compounds were capable of causing single-strand breaks in DNA macromolecules.

A one-pot method for the synthesis of 3-nitro-2H-thiopyrans starting from enamin-3-ones was developed. Reduction of the obtained 3-nitro-2H-thiopyrans with the benzaldehyde/o-phenylenediamine system in butanol led to 3-nitro-3,4-dihydro-2H-thiopyrans.

An effective and environmentally friendly technique for synthesizing hybrid molecules based on schizocommunin has been detailed in this study. This process involves a click reaction utilizing quinazolinones, isatin, and azides. Schizocommunin, a natural bioactive compound recognized for its wide array of biological functions including its anticancer properties, was employed as the foundational scaffold. The resultant triazo compounds originating from schizocommunin were subjected to thorough evaluation for their potential anticancer activity against three human cancer cell lines: MCF-7 (breast cancer), A549 (lung cancer), and PC-3 (prostate cancer), through employment of the MTT assay. One compound from the series showcased a remarkable anticancer efficacy (IC₅₀ 2.35 ± 0.67 μM) against MCF-7.