Radical Cascade Reaction of Heterocyclic Ketene Aminals with Thiocyanates Promoted by Visible Light: Synthesis of Functionalized Fused 2-Iminothiazolines DOI

Shu Shu Yang,

Tingting Guo, Jianbo Ma

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(18), P. 13678 - 13690

Published: Sept. 6, 2024

Herein, a visible-light-promoted radical cascade cyclization of heterocyclic ketene aminals (HKAs) and thiocyanates was developed to access functionalized fused 2-iminothiazolines. This novel reaction can be realized under only visible-light irradiation without the help external photocatalysts, oxidants, additives. These multicomponent reactions demonstrate excellent selectivity for

Language: Английский

Rh(III)-Catalyzed [3 + 2] Annulation/Pinacol Rearrangement Reaction of Enaminones with Iodonium Ylides: Direct Synthesis of 2-Spirocyclo-pyrrol-3-ones DOI

Mingshuai Zhang,

Longkun Chen,

Haifeng Sun

et al.

Organic Letters, Journal Year: 2023, Volume and Issue: 25(39), P. 7214 - 7219

Published: Sept. 26, 2023

A novel Rh(III)-catalyzed cascade alkenyl C-H activation/[3 + 2] annulation/pinacol rearrangement reaction of enaminones with iodonium ylides has been developed. This methodology provides a new and straightforward synthetic strategy to afford highly functionalized 2-spirocyclo-pyrrol-3-ones in satisfactory yield from readily available starting materials under mild conditions. Moreover, gram-scale reactions further derivatization experiments are implemented demonstrate the potential utility this developed approach.

Language: Английский

Citations

33

Photocatalytic Pyridine Synthesis with Enaminones and TMEDA under Metal-Free Conditions DOI

Junlong Zeng,

Tao Zhou, Jianchao Liu

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(15), P. 11060 - 11066

Published: July 24, 2024

Reported herein is a new photocatalytic annulation for the synthesis of 2,3,4,6-tetrasubstituted pyridines with enaminones and N,N,N′,N′-tetramethyl ethylenediamine (TMEDA). The reactions take place without requiring transition metal reagent provide products broad scope. methyl in TMEDA acts as carbon source pyridine ring construction, BrCF2CO2Et plays role terminal oxidant free radical quenching.

Language: Английский

Citations

7

Oxidative Free-Radical C(sp2)–H Bond Chlorination of Enaminones with LiCl: Access to Highly Functionalized α-Chlorinated Enaminones DOI

Yunhua Xie,

Zhilai Zhang,

Biao Zhang

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(12), P. 8521 - 8530

Published: June 3, 2024

An oxidative free-radical C(sp2)–H bond chlorination strategy of enaminones has been developed by using LiCl as a chlorinating reagent and K2S2O8 an oxidant. This transformation provides new straightforward synthetic methodology to afford highly functionalized α-chlorinated with Z-configuration in good excellent yields.

Language: Английский

Citations

6

Metal-free assembly of diverse polysubstituted pyridines via an efficient cascade approach using tertiary enaminones and α,β-unsaturated sulfonylketimines DOI
Xiang Li, Qiwen Pang, Yang Zhang

et al.

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(9), P. 2607 - 2612

Published: Jan. 1, 2024

A metal-free, scalable, and cascade protocol for assembling diverse polysubstituted pyridines from tertiary enaminones α,β-unsaturated sulfonylketimines by cleaving C–N/N–S bonds is reported.

Language: Английский

Citations

4

Copper(II)‐Catalyzed [2+2+2] Annulation of Enaminones with Maleimides Using a Traceless Directing Group Strategy DOI
Leiqing Fu, Hongxiang Huang, Yingying Jiang

et al.

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: 366(19), P. 4139 - 4144

Published: July 2, 2024

Abstract A copper‐catalyzed annulation of enaminones with maleimides was developed to synthesize various pyrrolo[3,4‐e]isoindoles. In this strategy, 2‐aminopyridine served as a traceless directing group, and target products were obtained in 54–72% yields. Moreover, plausible mechanism for reaction proposed based on several control experiments, deuterium exchange previous reports.

Language: Английский

Citations

3

Cycloaddition and Skeleton Rearrangement of Heterocyclic Ketene Aminals (HKAs) with 1-Diazonaphthalen-2(1H)-ones for the Synthesis of Functionalized 1,2,3-Triazoles DOI

Ke-Hua Zhao,

Jin-Mei Qi,

Xing-Mei Hu

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(32), P. 6866 - 6871

Published: Aug. 2, 2024

We developed a protocol for the synthesis of highly functionalized 5,6-dihydro-imidazo[1,2-

Language: Английский

Citations

1

Rhodium-catalyzed synthesis of N-substituted 3-acylpyrroles from enaminones and vinylene carbonate DOI
Jianbo Ma, Yiyong Yin,

Xing-Mei Hu

et al.

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: unknown

Published: Nov. 12, 2024

We developed a cascade C–H activation/[3 + 2] annulation for enaminones and vinylene carbonate, employing the catalyst [Cp*RhCl 2 ] oxidants. This reaction allows efficient synthesis of 3-carbonylpyrroles.

Language: Английский

Citations

1

Radical Cascade Reaction of Heterocyclic Ketene Aminals with Thiocyanates Promoted by Visible Light: Environmentally Fridendly Synthesis of Functionalized Fused 2-Iminothiazolines DOI

Shu Shu Yang,

Tingting Guo, Jianbo Ma

et al.

Published: Jan. 1, 2024

Download This Paper Open PDF in Browser Add to My Library Share: Permalink Using these links will ensure access this page indefinitely Copy URL DOI

Language: Английский

Citations

0

I2-Catalyzed cascade annulation of 2-(pyridin-2-yl)acetate derivatives with ,-dimethylenamine ketones: site-selective synthesis of functionalized indolizines DOI

Yuan-Da Li,

Weimin Zhang,

Ke-Hua Zhao

et al.

Tetrahedron, Journal Year: 2024, Volume and Issue: 159, P. 134015 - 134015

Published: May 3, 2024

Language: Английский

Citations

0

One-Pot Sequential Synthesis of Alkenylated Dihydroquinolinones and Hexahydroacridinones in Deep Eutectic Solvent Medium DOI Creative Commons

Sundararajan Suresh,

Fazlur‐Rahman Nawaz Khan

ACS Omega, Journal Year: 2024, Volume and Issue: unknown

Published: Aug. 16, 2024

The sequential synthesis of N-heterocycles from saturated ketones poses significant challenges and has rarely been reported. Herein, an efficient alkenylated dihydroquinolinones 7 hexahydroacridinones 8 is achieved 1 or 2 via dehydrogenation, cyclization, oxidation, α-alkenylation in choline chloride-based deep eutectic solvent (DES) medium. This strategy provides excellent yield low-cost, readily available starting materials under environmentally benign conditions. Furthermore, the synthesized compounds (4, 5, 7, 8) were investigated for their photophysical properties through absorption emission spectral studies.

Language: Английский

Citations

0