Synthesis of Isoquinolinediones via the Radical Addition/Cyclization of N‐Alkyl‐N‐methacryloylbenzamides with Monoalkyl Oxalates
Authors:
- 22 November 2023
- journal article
- research article
- Published by Wiley in Advanced Synthesis & Catalysis
- Vol. 365 (24) , 4527-4532
Abstract
A photocatalytic reaction of N‐alkyl‐N‐methacryloylbenzamides with monoalkyl oxalates is described. Monoalkyl oxalates undergo single‐electron oxidation/CO2 extrusion to generate alkoxycarbonyl radicals, followed by the addition and subsequent cyclization to give alkoxycarbonyl substituted isoquinolinediones. A wide variety of monoalkyl oxalates were amenable in this protocol, affording various alkoxycarbonyl substituted isoquinolinediones.Keywords
This publication has 30 references indexed in Scilit:
- Generation of the Methoxycarbonyl Radical by Visible-Light Photoredox Catalysis and Its Conjugate Addition with Electron-Deficient OlefinsOrganic Letters, 2016
- Aerobic oxidative cyclization of benzamides via meta-selective C–H tert-alkylation: rapid entry to 7-alkylated isoquinolinedionesChemical Communications, 2016
- Silver-Catalyzed Decarboxylative Addition/Cyclization of Activated Alkenes with Aliphatic Carboxylic AcidsThe Journal of Organic Chemistry, 2016
- Oxalates as Activating Groups for Alcohols in Visible Light Photoredox Catalysis: Formation of Quaternary Centers by Redox-Neutral Fragment CouplingJournal of the American Chemical Society, 2015
- Tetrabutylammonium Iodide-Catalyzed Radical Alkoxycarbonylation of Activated Alkenes: Synthesis of Isoquinolinedione DerivativesChinese Journal of Organic Chemistry, 2015
- Design, Synthesis, Biochemical, and Antiviral Evaluations of C6 Benzyl and C6 Biarylmethyl Substituted 2-Hydroxylisoquinoline-1,3-diones: Dual Inhibition against HIV Reverse Transcriptase-Associated RNase H and Polymerase with Antiviral ActivitiesJournal of Medicinal Chemistry, 2014
- Base-catalyzed bicyclization of dialkyl glutaconates with cinnamoylacetamides: a synthetic strategy for isoquinolinedione derivativesChemical Communications, 2014
- Metal‐Free Aryltrifluoromethylation of Activated AlkenesAngewandte Chemie International Edition, 2013
- 4-Substituted 2-Hydroxyisoquinoline-1,3(2H,4H)-diones as a Novel Class of HIV-1 Integrase InhibitorsACS Medicinal Chemistry Letters, 2013
- The design, synthesis and biological evaluations of C-6 or C-7 substituted 2-hydroxyisoquinoline-1,3-diones as inhibitors of hepatitis C virusBioorganic & Medicinal Chemistry, 2012