Synthesis of 4-Hydroxyindolin-2-ones via Phosphoric Acid-Mediated Annulation of β-Nitrostyrenes with
Haiwen Li1, Wenzhe Cheng1, Jiaman Lv1
1School of Chemistry and Chemical Engineering, Yangzhou University, 180 Siwangting Street, Yangzhou 225002, P. R. China.
Abstract:
The efficient synthesis of 4-hydroxy-3-arylindolin-2-ones via phosphoric acid-mediated annulation of various β-nitrostyrenes and 1,3-cyclohexanedione is described. This annulation reaction gives a practical method for affording a diverse set of oxindoles, having simple experimentation, readily available starting materials, and very good yields. Additionally, substituted 1,3-cyclohexanediones under the same conditions afforded tetrahydrobenzofuran oxime compounds.
More Related Videos
06:34Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides CHIPS
Published on: June 20, 2014
10:17Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones
Published on: February 7, 2019
Related Concept Videos
Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation
Cycloaddition Reactions: Overview
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction
Synthesis of α-Substituted Carbonyl Compounds: The Stork Enamine Reaction
Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation
One of the convenient methods for the preparation of aldehydes and ketones is via hydration of alkynes. Hydroboration-oxidation of alkynes is an indirect hydration reaction in which an alkyne is treated with borane followed by oxidation with alkaline peroxide to form an enol that rapidly converts into an aldehyde or a ketone. Terminal alkynes form aldehydes, whereas internal alkynes give ketones as the final product.
Preparation of Diols and Pinacol Rearrangement
The reaction begins with transferring a proton from the acid catalyst to one of the hydroxyl groups, producing an oxonium ion.
