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Regio‐ and Stereoselective Synthesis of 3‐Pyrazolylidene‐2‐oxindole Compounds by Nucleophilic Vinylic Substitution of ( E )‐3‐(Nitromethylene)indolin‐2‐one
Author(s) -
Vila Carlos,
Slack Sophie,
Blay Gonzalo,
Muñoz M. Carmen,
Pedro José R.
Publication year - 2019
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201900048
Subject(s) - chemistry , stereoselectivity , nucleophilic substitution , nucleophile , oxindole , pyrazolones , substitution reaction , stereochemistry , medicinal chemistry , organic chemistry , catalysis
A highly regio‐ and stereoselective synthesis of 3‐alkylidene‐2‐oxindoles has been described through a nucleophilic vinylic substitution (S N V) of ( E )‐3‐(nitromethylene)indolin‐2‐one using pyrazol‐3‐ones as nucleophiles and Et 3 N 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.