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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Construction of trifluoromethyl-containing heterocycles from trifluoroacetimidoyl chlorides and derivatives

Chemical Communications, Год журнала: 2023, Номер 59(33), С. 4872 - 4890

Опубликована: Янв. 1, 2023

Recent advances in the direct synthesis of trifluoromethyl-containing heterocycles from trifluoroacetimidoyl chlorides (TFAICs) and derivatives, including trifluoroacetimidohydrazides (TFAIHs) CF3-imidoyl sulfoxonium ylides (TFISYs), are systematically summarized discussed. The cascade annulation reactions synthons with suitable coupling partners have emerged as a powerful promising tool for construction variety trifluoromethyl-substituted heterocycles. Compared other building blocks, TFAICs derivatives notable merits easy availability handling, relative stability safety, high reactivity.

Язык: Английский

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OpenChemIE: An Information Extraction Toolkit for Chemistry Literature

Journal of Chemical Information and Modeling, Год журнала: 2024, Номер 64(14), С. 5521 - 5534

Опубликована: Июль 1, 2024

Information extraction from chemistry literature is vital for constructing up-to-date reaction databases data-driven chemistry. Complete requires combining information across text, tables, and figures, whereas prior work has mainly investigated extracting reactions single modalities. In this paper, we present OpenChemIE to address complex challenge enable the of data at document level. approaches problem in two steps: relevant individual modalities then integrating results obtain a final list reactions. For first step, employ specialized neural models that each specific task extraction, such as parsing molecules or text figures. We integrate these modules using chemistry-informed algorithms, allowing fine-grained condition substrate scope investigations. Our machine learning attain state-of-the-art performance when evaluated individually, meticulously annotate challenging dataset schemes with R-groups evaluate our pipeline whole, achieving an F1 score 69.5%. Additionally, accuracy 64.3% directly compared against Reaxys chemical database. most suited on organic literature, where are generally depicted planar graphs written can be consolidated into SMILES format. provide freely public open-source package, well through web interface.

Язык: Английский

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Regioselective Synthesis of 5-Trifluoromethyl 1,2,4-Triazoles via [3 + 2]-Cycloaddition of Nitrile Imines with CF3CN

Molecules, Год журнала: 2022, Номер 27(19), С. 6568 - 6568

Опубликована: Окт. 4, 2022

We herein describe a general approach to 5-trifluoromethyl 1,2,4-triazoles via the [3 + 2]-cycloaddition of nitrile imines generated in situ from hydrazonyl chloride with CF3CN, utilizing 2,2,2-trifluoroacetaldehyde O-(aryl)oxime as precursor trifluoroacetonitrile. Various functional groups, including alkyl-substituted chloride, were tolerated during cycloaddition. Furthermore, gram-scale synthesis and common downstream transformations proved potential synthetic relevance this developed methodology.

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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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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K₂CO₃-Catalyzed (3 + 2) Cycloaddition Reaction of N-2,2,2-Trifluoroethylisatin Ketimines with Azodicarboxylates: Access to Spirooxindoles Containing Trifluoromethyl-1,2,4-triazolines

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(4), С. 2364 - 2374

Опубликована: Фев. 7, 2024

Potassium carbonate-catalyzed (3 + 2) cycloaddition reaction between N-2,2,2-trifluoroethylisatin ketimines and azodicarboxylates has been developed, constructing a series of novel N-heterocycle infused spirooxindoles in good to excellent yields (up 98%) under milder conditions. The presence both biologically active oxindole trifluoromethyl-1,2,4-triazoline moieties these spirocyclic compounds would provide new lead structures the discovery heterocyclic with potential pharmaceutical activities.

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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Synthesis of trifluoromethyl formazans by reaction of trifluoromethyl N-acylhydrazones/N-Aryl hydrazones and aryldiazonium tetrafluoroborates

Journal of Fluorine Chemistry, Год журнала: 2023, Номер 272, С. 110211 - 110211

Опубликована: Ноя. 1, 2023

Язык: Английский

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Tandem Addition/Cyclization/Halogenation Reaction of Difluoromethylated N-Acylhydrazones with Allyltrimethylsilanes

The Journal of Organic Chemistry, Год журнала: 2023, Номер 88(24), С. 17356 - 17367

Опубликована: Дек. 6, 2023

As novel difluoromethyl building blocks, difluoromethylated N-acylhydrazones react with allyltrimethylsilanes and the halogen source via a tandem addition/cyclization/halogenation strategy, which produces various difluoromethylpyrazoline compounds in good yields. The method features mild reaction conditions, broad substrate scopes, transition metal-free process easy operation. It also proves that are useful blocks for construction of nitrogen heterocycles.

Язык: Английский

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