Regio- and Stereoselective Synthesis of 3-Pyrazolylidene-2-oxindole Compounds by Nucleophilic Vinylic Substitution of (E)-3-(Nitromethylene)indolin-2-one

Loading...
Thumbnail Image
Publication date
2019
Reading date
Journal Title
Journal ISSN
Volume Title
Publisher
Metrics
Export
Abstract
A highly regio- and stereoselective synthesis of 3-alkylidene-2-oxindoles has been described through a nucleophilic vinylic substitution (SNV) of (E)-3-(nitromethylene)indolin-2-one using pyrazol-3-ones as nucleophiles and Et3N as a base. The reaction affords selectively the Z-isomer when pyrazol-3-ones without substituents at the 4 position are used. While the reaction is E-selective with 4-substituted pyrazolones. The stereoselectivity (up to >20:1) and the yields (up to 98%) are very high under mild reaction conditions.
Description
Bibliographic reference
Vila Descals, Carlos Slack, Sophie Blay Llinares, Gonzalo Muñoz, M. Carmen Pedro, José Ramón 2019 Regio- and Stereoselective Synthesis of 3-Pyrazolylidene-2-oxindole Compounds by Nucleophilic Vinylic Substitution of (E)-3-(Nitromethylene)indolin-2-one Advanced Synthesis & Catalysis 361 8 1902 1907
Collections