6533b824fe1ef96bd128012f
RESEARCH PRODUCT
Regio- and Stereoselective Synthesis of 3-Pyrazolylidene-2-oxindole Compounds by Nucleophilic Vinylic Substitution of (E)-3-(Nitromethylene)indolin-2-one
M. Carmen MuñozSophie SlackCarlos VilaGonzalo BlayJosé R. Pedrosubject
010405 organic chemistryChemistryStereochemistryEstereoquímica2-oxindoleSubstitution (logic)2-oxindoleStereoselectivityGeneral ChemistryIndolin 2 one010402 general chemistry01 natural sciences0104 chemical sciencesReaccions químiquesRegioselectivityNucleophileFISICA APLICADAmedia_common.cataloged_instancePyrazoloneStereoselectivityEuropean unionmedia_commonVinylic substitutiondescription
[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.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2019-01-01 |