Additive‐free and Diastereoselective Synthesis for trans‐Disubstituted‐2,3‐dihydro‐benzofurans via [4 + 1] Annulation between p‐QMs and TFISYs DOI
Yong Li,

Chuan‐Chuan Wang,

Mengru Ren

et al.

European Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Oct. 14, 2024

Abstract An additive‐free and diastereoselective [4+1] annulation between ortho ‐hydroxyphenyl‐substituted para ‐quinone methides CF 3 ‐substituted imidoyl sulfoxonium ylides is developed, providing a facile practical route to diverse trans ‐2,3‐dihydrobenzofurans with high efficiency. This protocol features mild conditions, broad substrate scope easy operate.

Language: Английский

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

Yaopeng Liu,

Qingyu Tian,

Jin Ge

et al.

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: 22(31), P. 6246 - 6276

Published: Jan. 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.

Language: Английский

Citations

12
Copper-Catalyzed One-Pot Synthesis of Thiazolidin-2-imines DOI Creative Commons
Leandros P. Zorba,

Ioannis Stylianakis,

Nikolaos Tsoureas

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(11), P. 7727 - 7740

Published: May 10, 2024

The synthesis of thiazolines, thiazolidines, and thiazolidinones has been extensively studied, due to their biological activity related neurodegenerative diseases, such as Parkinson's Alzheimer's, well antiparasitic antihypertensive properties. closely thiazolidin-2-imines have studied less, efficient strategies for synthesizing them, mainly based on the reaction propargylamines with isothiocyanates, explored less. use one-pot approaches, providing modular, straightforward, sustainable access these compounds, also received very little attention. Herein, we report a novel, one-pot, multicomponent, copper-catalyzed among primary amines, ketones, terminal alkynes, toward bearing quaternary carbon centers five-membered ring, in good excellent yields. Density functional theory calculations, combined experimental mechanistic findings, suggest that copper(I)-catalyzed between situ-formed isothiocyanates proceeds lower energy barrier pathway leading S-cyclized product, compared N-cyclized one, chemo- regioselective formation 5-exo-dig thiazolidin-2-imines.

Language: Английский

Citations

4
Lithium Bromide-Promoted Formal C(sp3)–H Bond Insertion Reactions of β-Carbonyl Esters with Sulfoxonium Ylides to Synthesize 1,4-Dicarbonyl Compounds DOI

Hailin Guo,

Yuhao Ding,

Jingwen Fan

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(10), P. 6974 - 6986

Published: May 4, 2024

A LiBr-promoted formal C(sp3)–H bond insertion reaction between β-carbonyl esters and sulfoxonium ylides is established. This practical has a wide range of substrate scope for both to give variety 1,4-dicarbonyl compounds with 43–94% yields. The features transition-metal-free conditions exclusive C-alkylation chemselectivity. use bench-stable overcomes previous methods that require transition metal as catalysts unstable diazo or toxic haloketones alkylation reagents.

Language: Английский

Citations

2
Base‐Mediated Cascade Reaction of CF3‐Imidoyl Sulfoxonium Ylides and Diimides for the Synthesis of Functionalized Amidines DOI

Sihao Ling,

Qihua Chen, Zhengkai Chen

et al.

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: unknown

Published: Oct. 7, 2024

Abstract A base‐mediated cascade reaction of CF 3 ‐imidoyl sulfoxonium ylides (TFISYs) and diimides has been developed for the preparation functionalized amidines. In transformation, a nucleophilic addition subsequent [2,3]‐sigmatropic rearrangement ylide occur to enable an intramolecular migration dimethyl sulfoxide (DMSO). The unexpected result protocol demonstrates chameleonic reactivity TFISYs.

Language: Английский

Citations

1
Synthesis of N-Aryl-4-trifluoromethylthiazol-2-amines via Insertion/Annulation of Trifluoromethylimidoyl Sulfoxonium Ylides with Sodium Thiocyanate DOI

Yuhao Ding,

Yaopeng Liu,

Jin Ge

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(17), P. 12255 - 12262

Published: Aug. 16, 2024

An efficient p-TsOH-mediated insertion of sodium thiocyanate into trifluoromethylimidoyl sulfoxonium ylides has been reported, affording annulated N-aryl-4-trifluoromethylthiazol-2-amines in 42–84% yields a one-pot manner. This protocol encompasses variety with serving as the source "S–C═N" moiety thiazole ring. The versatile transformations resulting pharmacologically important were also demonstrated.

Language: Английский

Citations

0
Additive‐free and Diastereoselective Synthesis for trans‐Disubstituted‐2,3‐dihydro‐benzofurans via [4 + 1] Annulation between p‐QMs and TFISYs DOI
Yong Li,

Chuan‐Chuan Wang,

Mengru Ren

et al.

European Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Oct. 14, 2024

Abstract An additive‐free and diastereoselective [4+1] annulation between ortho ‐hydroxyphenyl‐substituted para ‐quinone methides CF 3 ‐substituted imidoyl sulfoxonium ylides is developed, providing a facile practical route to diverse trans ‐2,3‐dihydrobenzofurans with high efficiency. This protocol features mild conditions, broad substrate scope easy operate.

Language: Английский

Citations

0