Metal-free C3–H acylation of quinoxalin-2(1H)-ones with α-oxo-carboxylic acids
- 11 August 2020
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Organic & Biomolecular Chemistry
- Vol. 18 (33) , 6558-6563
Abstract
Direct C3–H acylation of quinoxalin-2(1H)-ones with α-oxocarboxylic acids under thermo conditions promoted by PIDA has been achieved in a moderate to good yield in a very fast manner. Mechanistic study revealed that the reaction proceeds via a radical process. In addition, this method could be applied to a gram-scale reaction and antitumor agent synthesis. This work represents a simple, convenient and efficient synthesis of 3-acylated quinoxalin-2(1H)-ones.Keywords
This publication has 50 references indexed in Scilit:
- Transition Metal‐Free Iodosobenzene‐Promoted Direct Oxidative 3‐Arylation of Quinoxalin‐2(H)‐ones with ArylhydrazinesAdvanced Synthesis & Catalysis, 2017
- Photoredox‐Catalysed Decarboxylative Alkylation of N‐Heteroarenes with N‐(Acyloxy)phthalimidesChemistry – A European Journal, 2017
- Photoredox/Brønsted Acid Co-Catalysis Enabling Decarboxylative Coupling of Amino Acid and Peptide Redox-Active Esters with N-HeteroarenesACS Catalysis, 2016
- Copper-catalysed oxidative amination of quinoxalin-2(1H)-ones with aliphatic aminesOrganic & Biomolecular Chemistry, 2016
- Direct phosphonation of quinoxalin-2(1H)-ones under transition-metal-free conditionsChemical Communications, 2016
- Decarboxylative 1,4-Addition of α-Oxocarboxylic Acids with Michael Acceptors Enabled by Photoredox CatalysisOrganic Letters, 2015
- Assisted Tandem Palladium(II)/Palladium(0)‐Catalyzed C‐ and N‐Arylations of Quinoxalin‐2(1 H)‐ones in WaterAdvanced Synthesis & Catalysis, 2014
- Synthesis of (E)-1,1-Diethoxy-3-(3-hydroxy-3-arylfuro[2,3-b]quinoxalin-2(3H)-ylidene)propan-2-ones via Acid-Catalyzed, Stereoselective 5-Exo-DigCyclizationJournal of Heterocyclic Chemistry, 2014
- Palladium(II)-Catalyzed Oxidative Arylation of Quinoxalin-2(1H)-ones with Arylboronic AcidsOrganic Letters, 2013
- Discovery of potent pteridine reductase inhibitors to guide antiparasite drug developmentProceedings of the National Academy of Sciences, 2008