Uses
A versatile reactant. As 3-Methylindole metabolite. Reactant for enantioselective α-amination reactions, Reactant for aldol reaction with glyoxal derivatives, Reactant for amine thiourea catalyzed conjugate addition to α,β-unsaturated aldehydes, Reactant for O-acetylation reactions, Reactant for preparation of a disubstituted oxoindole by using rhodium-catalyzed cyclopropanation/ring-opening reactions.
Uses
• ;Reactant for enantioselective α-amination reactions1• ;Reactant for aldol reaction with glyoxal derivatives2• ;Reactant for amine thiourea catalyzed conjugate addition to α,β-unsaturated aldehydes3• ;Reactant for O-acetylation reactions4• ;Reactant for preparation of a disubstituted oxoindole by using rhodium-catalyzed cyclopropanation/ring-opening reactions5
Definition
ChEBI: 3-methyloxindole is a member of the class of oxindoles that is oxindole (1,3-dihydro-2H-indol-2-one) in which one of the hydrogens at position 3 has been replaced by a methyl group. It is a member of oxindoles and a methylindole.
General Description
3-Methyl-2-oxindole (MOI) is a 3-substituted-2-oxindole. It is reported to be formed during the oxidation of indole-3-acetic acid in the presence of Fe
II under aerobic conditions. MOI undergoes asymmetric
anti-Mannich-type reaction with
N-tosyl aryl aldimines in the presence of alkaloid cinchona derivatives to form anti-3,3-disubsituted 2-oxindole derivatives. It also undergoes asymmetric hydroxyamination with nitrosoarenes to form
N-nitroso aldol products.
Synthesis
3-Methylhydroxyindole can be prepared from -chloropropionyl chloride and aniline in two steps.
