Synthesis of (E)-Quinoxalinone Oximes through a Multicomponent Reaction under Mild Conditions DOI
Jun Xu,

Huiyong Yang,

Lei He

et al.

Organic Letters, Journal Year: 2020, Volume and Issue: 23(1), P. 195 - 201

Published: Dec. 23, 2020

Herein, a novel method for the gram-scale synthesis of (E)-quinoxalinone oximes through multicomponent reaction under mild conditions is described. Such transformation was performed transition-metal-free conditions, affording (E)-oximes in moderate-to-good yield recrystallization. Our methodology demonstrates successful combination Mannich-type and radical coupling, providing green practical approach potentially bioactive quinoxalinone-containing molecules.

Language: Английский

Enantioselective Chemodivergent Three-Component Radical Tandem Reactions through Asymmetric Photoredox Catalysis DOI

Chaorui Ma,

Jingyu Shen,

Chaofan Qu

et al.

Journal of the American Chemical Society, Journal Year: 2023, Volume and Issue: 145(36), P. 20141 - 20148

Published: Aug. 28, 2023

Chemodivergent synthesis has been achieved in asymmetric photocatalysis. Under a dual catalyst system consisting of chiral phosphoric acid and DPZ as photosensitizer, different inorganic bases enabled the formation two sets valuable products from three-component radical tandem transformations 2-bromo-1-arylenthan-1-ones, styrenes, quinoxalin-2(1H)-ones. The key to success was distinct pKa environment, which radicals that formed on quinoxalin-2(1H)-one rings after addition processes underwent either single-electron oxidation or reduction. In addition, this work represents first use quinoxalin-2(1H)-ones photoredox catalysis.

Language: Английский

Citations

29

Piezocatalyzed Decarboxylative Acylation of Quinoxalin-2(1H)-ones Using Ball Milling DOI
Yu He, Gefei Wang, Wenbo Hu

et al.

ACS Sustainable Chemistry & Engineering, Journal Year: 2023, Volume and Issue: 11(3), P. 910 - 920

Published: Jan. 11, 2023

The first piezochemically driven decarboxylative coupling of the C–H bond was developed. agitation BaTiO3 via ball milling converts mechanical energy into electrical potential, leading to production a benzoyl radical single-electron transfer pathway analogous photocatalytic reaction. This mechanoredox catalytic strategy synthesize C3-acylated quinoxalin-2(1H)-ones requires no solvent, short reaction time, and simple handling skills, exhibiting promising potential in large-scale chemical manufacturing.

Language: Английский

Citations

28

Photoinduced Decarboxylative C3–H Alkylation of Quinoxalin-2(1H)-ones DOI

Akash Bisoyi,

Alisha Rani Tripathy,

Girish Suresh Yedase

et al.

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(4), P. 2631 - 2641

Published: Feb. 3, 2023

An efficient, catalyst- and additive-free, visible-light-driven radical C3-H alkylation of quinoxalin-2(1H)-one derivatives has been developed. This reaction utilizes alkyl-NHP-esters as an alkyl donor acceptor. The operationally simple protocol works under mild conditions tolerates a variety functional groups. Furthermore, the synthetic utility methodology was successfully implemented for synthesizing biologically relevant C3-alkyl substituted derivatives.

Language: Английский

Citations

28

Photochemical and Electrochemical Synthesis of Oxazoles and Isoxazoles: An Update DOI
Debashis Ghosh,

Ancy Sherin,

Sumit Ghosh

et al.

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: 366(10), P. 2186 - 2208

Published: April 4, 2024

Abstract This review presents an outline of current advancements in the photochemical and electrochemical synthesis oxazoles isoxazoles. Oxazole isoxazole are important building blocks for a variety medicinally useful compounds. Therefore, these heterocycles via sustainable technologies is worth demanding. Photochemical two among few technologies. covers brief discussion on reaction parameters like catalysts, substrates scope, temperature, solvents, electrodes, electrolytes (in case process), light source process) individual reaction. Detailed mechanistic insight each also presented. Finally, summary, future direction toward development effective methods isoxazoles

Language: Английский

Citations

11

Synthesis of (E)-Quinoxalinone Oximes through a Multicomponent Reaction under Mild Conditions DOI
Jun Xu,

Huiyong Yang,

Lei He

et al.

Organic Letters, Journal Year: 2020, Volume and Issue: 23(1), P. 195 - 201

Published: Dec. 23, 2020

Herein, a novel method for the gram-scale synthesis of (E)-quinoxalinone oximes through multicomponent reaction under mild conditions is described. Such transformation was performed transition-metal-free conditions, affording (E)-oximes in moderate-to-good yield recrystallization. Our methodology demonstrates successful combination Mannich-type and radical coupling, providing green practical approach potentially bioactive quinoxalinone-containing molecules.

Language: Английский

Citations

69