0000000001308625
AUTHOR
Sophie Slack
Regio- and Stereoselective Synthesis of 3-Pyrazolylidene-2-oxindole Compounds by Nucleophilic Vinylic Substitution of (E)-3-(Nitromethylene)indolin-2-one
[EN] 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.
CCDC 1889981: Experimental Crystal Structure Determination
Related Article: Carlos Vila, Sophie Slack, Gonzalo Blay, M. Carmen Muñoz, José R. Pedro|2019|Adv.Synth.Catal.|361|1902|doi:10.1002/adsc.201900048
CCDC 1890014: Experimental Crystal Structure Determination
Related Article: Carlos Vila, Sophie Slack, Gonzalo Blay, M. Carmen Muñoz, José R. Pedro|2019|Adv.Synth.Catal.|361|1902|doi:10.1002/adsc.201900048