Cobalt-Catalyzed Tandem Transformation of 2-Aminobenzonitriles to Quinazolinones Using Hydration and Dehydrogenative Coupling Strategy
- 4 September 2020
- journal article
- research article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 85 (17), 11359-11367
- https://doi.org/10.1021/acs.joc.0c01307
Abstract
A tandem synthesis of quinazolinones from 2-aminobenzonitriles is demonstrated here by using an aliphatic alcohol-water system. For this transformation, a cheap and easily available cobalt salt and P(CH2CH2PPh2)(3)(PP3) ligand were employed. The substrate scope, scalability, and synthesis of natural products exhibited the vitality of this protocol.Funding Information
- Science and Engineering Research Board
- Council of Scientific & Industrial Research
This publication has 41 references indexed in Scilit:
- Cu(II)–Glucose: Sustainable Catalyst for the Synthesis of Quinazolinones in a Biomass-Derived Solvent 2-MethylTHF and Application for the Synthesis of DiproqualoneACS Sustainable Chemistry & Engineering, 2018
- Divergent Synthesis of Quinazolin-4(3H)-ones and Tryptanthrins Enabled by a tert-Butyl Hydroperoxide/K3PO4-Promoted Oxidative Cyclization of Isatins at Room TemperatureOrganic Letters, 2016
- Recent Advances in α-Alkylation Reactions using Alcohols with Hydrogen Borrowing MethodologiesACS Catalysis, 2014
- Recent advances in the structural library of functionalized quinazoline and quinazolinone scaffolds: Synthetic approaches and multifarious applicationsEuropean Journal of Medicinal Chemistry, 2014
- Palladium‐Catalyzed Carbonylative Synthesis of Quinazolinones from 2‐Aminobenzamide and Aryl BromidesChemistry – A European Journal, 2013
- Synthesis, anti-inflammatory evaluation and docking studies of some new fluorinated fused quinazolinesEuropean Journal of Medicinal Chemistry, 2010
- Dehydrogenation as a Substrate-Activating Strategy in Homogeneous Transition-Metal CatalysisChemical Reviews, 2009
- Highly efficient copper-catalyzed cascade synthesis of quinazoline and quinazolinone derivativesChemical Communications, 2008
- Quinoline, quinazoline and acridonealkaloidsNatural Product Reports, 2007
- A Novel One‐Pot Synthesis of 2‐Aryl‐4(3H)‐Quinazolinones Using Room Temperature Ionic Liquid as Reaction Medium as well as PromoterSynthetic Communications, 2005