Recent advances in the synthesis of trifluoromethyl-containing heterocyclic compounds via trifluoromethyl building blocks

Organic & Biomolecular Chemistry, Год журнала: 2024, Номер 22(31), С. 6246 - 6276

Опубликована: Янв. 1, 2024

Recent advances in the preparation of trifluoromethyl-containing heterocyclics via trifluoromethyl building block strategies over period from 2019 to present are systematically summarized and discussed.

Язык: Английский

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[3 + 2] Cycloaddition Reaction of Vinylsulfonium Salts with Hydrazonoyl Halides: Synthesis of Pyrazoles

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(14), С. 10066 - 10076

Опубликована: Июль 2, 2024

An efficient [3 + 2] cycloaddition reaction between in situ generated nitrile imines from hydrazonoyl halides and vinylsulfonium salts is developed. The are demonstrated to be a new class of partner for conduct the reaction. process provides concise method construction pyrazole derivatives under mild conditions with broad substrate scope, good product yields, high regioselectivity.

Язык: Английский

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Trifluoromethyl N-acylhydrazones: A versatile trifluoromethyl building blocks for construction of trifluoromethylated nitrogen-containing compounds

Tetrahedron, Год журнала: 2024, Номер 154, С. 133870 - 133870

Опубликована: Фев. 6, 2024

Язык: Английский

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Synthesis of fused 3-trifluoromethyl-1,2,4-triazoles via base-promoted [3 + 2] cycloaddition of nitrile imines and 1H-benzo[d]imidazole-2-thiols

Organic & Biomolecular Chemistry, Год журнала: 2023, Номер 21(35), С. 7095 - 7099

Опубликована: Янв. 1, 2023

Here we report a strategy for the facile assembly of fused 3-trifluoromethyl-1,2,4-triazoles, which are difficult to synthesize using traditional strategies, in 50-96% yields through triethylamine-promoted intermolecular [3 + 2] cycloaddition pathway. This protocol features high efficiency, good functional group tolerance, mild conditions, and easy operation. Furthermore, gram-scale reaction product derivatizations were carried out smoothly illustrate practicability this method.

Язык: Английский

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Synthesis of ring fused difluoromethyl pyrazolines and pyrazoles by cycloaddition of difluoroacetohydrazonoyl bromides with cyclic α,β-Unsaturated carbonyl compounds

Tetrahedron, Год журнала: 2023, Номер 149, С. 133711 - 133711

Опубликована: Окт. 20, 2023

Язык: Английский

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Trifluoromethylated hydrazones and acylhydrazones as potent nitrogen-containing fluorinated building blocks

Beilstein Journal of Organic Chemistry, Год журнала: 2023, Номер 19, С. 1741 - 1754

Опубликована: Ноя. 15, 2023

Nitrogen-containing organofluorine derivatives, which are prepared using fluorinated building blocks, among the most important active fragments in various pharmaceutical and agrochemical products. This review focuses on reactivity, synthesis, applications of fluoromethylated hydrazones acylhydrazones. It summarizes recent methodologies that have been used for synthesis nitrogen-containing compounds.

Язык: Английский

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Trapping in situ generated CF₃-nitrile imines with maleimides under solvent-free mechanochemical conditions

RSC Mechanochemistry, Год журнала: 2024, Номер unknown

Опубликована: Янв. 1, 2024

A series of trifluoromethylated pyrrolo[3,4- c ]pyrazoles were obtained via mechanochemical (3 + 2)-cycloaddition in situ generated trifluoroacetonitrile imines with maleimide and its N -aliphatic/aromatic analogues.

Язык: Английский

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Green Oxidation of Heterocyclic Ketones with Oxone in Water

The Journal of Organic Chemistry, Год журнала: 2023, Номер 88(21), С. 15461 - 15465

Опубликована: Окт. 12, 2023

The recently reported efficient conversion of cyclic ketones to lactones by Oxone in neutral buffered water is extended heterocyclic ketones, namely, N-Boc azaketones and oxoethers with the aim obtaining N-protected azalactones their analogues oxygen place nitrogen. N-Boc-4-piperidinone all were successfully oxidized lactones, while azacyclic nitrogen α-positioned carbonyl univocally transformed into N-Boc-ω-amino acids N-Boc-N-formyl-ω-amino operating alkaline DMF, respectively.

Язык: Английский

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ω-(3-Trifluoromethylpyrazol-4-yl)alkanoic acids via (3 + 2)-cycloaddition of nitrile imines with cyclic enones and deacylative aromatization

Journal of Fluorine Chemistry, Год журнала: 2023, Номер 272, С. 110206 - 110206

Опубликована: Окт. 19, 2023

Язык: Английский

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The cyclization/rearrangement of α-hydroxy ketones with trifluoromethyl N-acylhydrazones to synthesize multi-substituted trifluoromethyloxazolines

Chemical Communications, Год журнала: 2023, Номер 59(96), С. 14293 - 14296

Опубликована: Янв. 1, 2023

A highly efficient and metal-free [3+2] cyclization/rearrangement reaction toward the synthesis of multisubstituted trifluoromethyloxazolines from α-hydroxyketones trifluoromethyl N-acylhydrazones has been developed. The unprecedented rearrangement amide fragment under acidic conditions after cleavage N-N bond acylhydrazones opened up new avenues for development reactions involving N-acylhydrazones. DFT calculations show that mechanism involves multiple proton transfer processes.

Язык: Английский

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