Electrochemical Enaminone-Thioamide Annulation and Thioamide Dimeric Annulation for the Tunable Synthesis of Thiazoles and 1,2,4-Thiadiazole

Organic Letters, Год журнала: 2024, Номер 26(25), С. 5263 - 5268

Опубликована: Июнь 14, 2024

A green and sustainable electrochemical oxidative cyclization of enaminones with thioamides under metal- oxidant-free conditions has been developed, providing an efficient approach for thiazole synthesis. Furthermore, 1,2,4-thiadiazoles can be selectively accessed via the dimerization in absence enaminones.

Язык: Английский

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Recent advances in transition metal-catalyzed transformations in N,N-disubstituted enaminones

Tetrahedron Letters, Год журнала: 2023, Номер 130, С. 154766 - 154766

Опубликована: Сен. 26, 2023

Язык: Английский

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HFIP-Mediated Multicomponent Reactions: Synthesis of Pyrazole-Linked Thiazole Derivatives

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(7), С. 4423 - 4437

Опубликована: Март 14, 2024

The development of one-pot, atom, and step-economic new methods avoiding metal, harsh reaction conditions, toxic reagents for the synthesis medicinally important hybrid molecules bearing more than one bioactive moieties is currently hot topics in organic synthesis. Herein, we report a green efficient room temperature multicomponent novel pyrazole-linked thiazoles involving one-pot C–C, C–N, C–S bond-forming process from aryl glyoxal, thioamide, pyrazolones 1,1,1,3,3,3-hexafluoroisopropanol, hydrogen bond donating medium. A set diverse thiazole pyrazole were prepared good to excellent yields by using this method. This methodology can also be extended prepare thiazole-linked barbiturates as well imidazole-linked pyrazoles. All products fully characterized spectroscopic techniques. notable features protocol are temperature, metal additive-free use recyclable solvent, water byproduct, wide substrate scope, operational simplicity, easy purification, applicability gram-scale synthesis, high atom economy, presence two products.

Язык: Английский

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Self‐ or Acridinium‐Catalyzed Electrophotosynthesis of Thiocyanato Heterocycles from Activated Alkenes

Advanced Synthesis & Catalysis, Год журнала: 2024, Номер 366(10), С. 2352 - 2362

Опубликована: Апрель 5, 2024

Abstract While the emergence of electrophotochemistry provides opportunities, such a chemistry at this stage suffers from limited reaction types and high photocatalyst loadings. A self‐catalyzed electrophotosynthesis as well one with low loading is presented. These external‐oxidant‐free cyclizations are enabling applicable to range activated alkenes, affording diverse array thiocyanato heterocycles including 4‐pyrrolin‐2‐ones, isoquinoline‐1,3‐diones, indolo[2,1‐ ]isoquinolin‐6(5 H )‐ones, benzoimidazo[2,1‐ )‐ones indolin‐2‐ones, protocols amenable late‐stage diversification complex molecular architectures gram‐scale syntheses. Sunlight could serve light source, be conducted in an all‐solar‐driven mode using commercially available photovoltaic panel produce electricity.

Язык: Английский

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Photocatalytic Annulation of Enaminones with Thioureas for the Synthesis of 2-Aminothiazoles via Tandem C–S and C–N Bond Formation

Synthesis, Год журнала: 2024, Номер 56(16), С. 2565 - 2571

Опубликована: Апрель 26, 2024

Abstract Visible-light photocatalytic reactions between enaminones and thioureas leading to thiazole products have been achieved. The annulation process consists of tandem C–S C–N bond formation by running under air atmosphere at ambient temperature. Broad substrate tolerance the sustainable protocol has verified practical synthesis divergent thiazoles with both monocyclic fused cyclic structures.

Язык: Английский

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Electrosynthesis of N/S-Heterocycles

Green Chemistry, Год журнала: 2024, Номер 26(13), С. 7532 - 7551

Опубликована: Янв. 1, 2024

In this review, we present a comprehensive overview of our recent advancements in the methodology electrochemically assisted radical generation and its subsequent application synthesis functionalization diverse N/S-heterocyclic compounds.

Язык: Английский

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Electro-Oxidative Three-Component Synthesis of 3,5-Disubstituted-1,2,4-Thiadiazoles from Amines, Amidines, and CS₂

The Journal of Organic Chemistry, Год журнала: 2025, Номер unknown

Опубликована: Март 29, 2025

1,2,4-Thiadiazoles, a significant class of heterocyclic compounds, are widely found in biologically active molecules. Herein, we report green electrochemical three-component reaction amines, amidines, and CS2 for the effective synthesis 3,5-disubstituted-1,2,4-thiadiazoles under metal- oxidant-free conditions. Both aliphatic aryl amines well-tolerated at room temperature simple undivided cell. A series 1,2,4-thiadiazoles prepared with excellent functional groups.

Язык: Английский

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Recent Advances in Site Selective Transformations of β-Enaminones via C-H Functionalization/Annulation

Organic & Biomolecular Chemistry, Год журнала: 2024, Номер unknown

Опубликована: Янв. 1, 2024

β-Enaminone transformation strategies are widely employed in the synthesis of numerous biologically active drugs and natural products, highlighting their significance medicinal chemistry.

Язык: Английский

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I₂-Induced Umpolung: Synthesis of a 1,6-Dihydrofuro[3,2-b]pyrazolo[3,4-e][1,4]thiazine Skeleton via an Unconventional 1,4-Dithiane-2,5-diol Reaction Mode

Organic Letters, Год журнала: 2024, Номер 26(37), С. 7891 - 7896

Опубликована: Сен. 6, 2024

In this paper, novel sulfur-containing 1,6-dihydrofuro[3,2-

Язык: Английский

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Divergent Synthesis of Enynals and Dihydrobenzo[f]isoquinolines via Deoxyalkynylation of Enaminones Enabled by the Cooperative Action of Tf₂O/Pd/Cu

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(22), С. 16419 - 16425

Опубликована: Окт. 28, 2024

A variety of enynals and dihydrobenzo[

Язык: Английский

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