Photoinduced Deaminative Alkylation of Quinoxalin‐2(1H)‐ones via an Electron Donor‐Acceptor Complex DOI

Haoran Jiao,

Kaikai Niu, Hongjian Song

et al.

ChemistrySelect, Journal Year: 2023, Volume and Issue: 8(25)

Published: July 3, 2023

Abstract Formation of C−C bonds by cleavage the C(sp 3 )−N readily available alkyl amines is a valuable transformation. Herein, we report method for oxidant‐ and metal‐free photoinduced deaminative alkylation quinoxalin‐2(1 H )‐ones with Katritzky salts as radical sources. Various radicals could easily be generated single‐electron reduction electron donor–acceptor complexes between sodium acetate. This green, sustainable, operationally simple has broad substrate scope, can used gram‐scale synthesis, late‐stage modification pharmaceutically relevant molecules.

Language: Английский

Three‐Component Reactions of Quinoxalin‐2(1H)‐ones: Recent Advances DOI Open Access
Keli Wang,

Hong‐Tao Ji,

Li‐Juan Ou

et al.

European Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: unknown

Published: Sept. 11, 2023

Abstract The multicomponent reactions of quinoxalin‐2(1 H )‐ones has attracted considerable interest due to their significant biological and chemical activities. very recent advances (from 2021 the beginning 2023) on radical three‐component cascade reaction )‐one derivatives at C3 position were summarized in this mini‐review. According kind types involved, some representative examples detailed mechanism have been categorized discussed. red front was covered by Figure 1.

Language: Английский

Citations

36
Sono-photocatalytic amination of quinoxalin-2(1H)-ones with aliphatic amines DOI
Wen‐Tao Ouyang,

Jun Jiang,

Yanfang Jiang

et al.

Chinese Chemical Letters, Journal Year: 2024, Volume and Issue: 35(10), P. 110038 - 110038

Published: May 22, 2024

Language: Английский

Citations

15
Photoredox-Catalyzed Three-Component Amidoheteroarylation of Unactivated Alkenes DOI
Mengxuan Zhang, Ji Zhang, Yuchen Zhou

et al.

Organic Letters, Journal Year: 2023, Volume and Issue: 25(22), P. 4113 - 4118

Published: May 30, 2023

A photoredox-catalyzed 1,2-amidoheteroarylation of unactivated alkenes with O-acyl hydroxylamine derivatives and heterocycles is presented. range heterocycles, including quinoxaline-2(1H)-ones, azauracils, chromones, quinolones, are capable for this process, allowing the direct synthesis valuable heteroarylethylamine derivatives. Structurally diverse reaction substrates, drug-based scaffolds, were successfully applied, demonstrating practicality method.

Language: Английский

Citations

19
Visible-Light-Promoted Deoxygenative Alkylation of Quinoxalin-2(1H)-ones with Activated Alcohols DOI

Lili Wang,

Pengyuan Yang, Jinwei Yuan

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(9), P. 6334 - 6344

Published: April 15, 2024

A one-pot strategy for deoxygenative alkylation of alcohols with quinoxalin-2(1H)-ones was developed by using xanthate salts as alcohol-activating groups radical generation in the presence tricyclohexylphosphine under visible-light-promoted conditions. The remarkable features this reaction include a broad substrate scope, excellent functional group tolerance, mild conditions, and simple operation. Moreover, synthetic utility validated success two-step reactions, scale-up synthesis, chemoselective monodeoxygenation diols.

Language: Английский

Citations

5
Visible‐Light‐Induced Metal‐Free Three‐Component Amidoheteroarylation of Alkenes to Synthesize β‐(Hetero)arylethylamines DOI

Qiange Feng,

He Wang, Yang Liu

et al.

European Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 27(19)

Published: March 21, 2024

Abstract Herein, visible‐light‐induced metal‐free three‐component amidoheteroarylation of alkenes with quinoxalin‐2(1 H )‐ones and N‐sulfonylaminopyridinium salts is developed. This protocol involves a radical relay process in which the N‐centered radicals undergo chemoselective addition to form an alkyl that selectively combines heteroarenes, leading formation C−C C−N bonds one step under mild reaction conditions. The involved high efficiency selectivity, wide substrate scope, excellent functional‐group compatibility demonstrate practicability developed protocol.

Language: Английский

Citations

3
Photocatalytic Three‐Component α‐Trifluoroalkyl‐β‐heteroarylation of Unactivated Alkenes with Trifluoroacetates DOI
Yang He, Wenlin Wang, Yuanyuan An

et al.

European Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 27(27)

Published: May 23, 2024

Abstract We herein disclose a direct and practical photocatalytic three‐component α‐trifluoroalkyl‐β‐heteroarylation of various unactivated alkenes with trifluoroacetates quinoxalin‐2(1 H )‐ones. The reaction takes place via photoinduced LMCT process, allowing efficient synthesis variety 3‐fluoroalkylated )‐one derivatives in moderate to excellent yields under mild conditions.

Language: Английский

Citations

1
Photoinduced Deaminative Alkylation of Quinoxalin‐2(1H)‐ones via an Electron Donor‐Acceptor Complex DOI

Haoran Jiao,

Kaikai Niu, Hongjian Song

et al.

ChemistrySelect, Journal Year: 2023, Volume and Issue: 8(25)

Published: July 3, 2023

Abstract Formation of C−C bonds by cleavage the C(sp 3 )−N readily available alkyl amines is a valuable transformation. Herein, we report method for oxidant‐ and metal‐free photoinduced deaminative alkylation quinoxalin‐2(1 H )‐ones with Katritzky salts as radical sources. Various radicals could easily be generated single‐electron reduction electron donor–acceptor complexes between sodium acetate. This green, sustainable, operationally simple has broad substrate scope, can used gram‐scale synthesis, late‐stage modification pharmaceutically relevant molecules.

Language: Английский

Citations

1