1997
Chemoselective intramolecular annulation of 3-alkylindolines into dihydro or tetrahydrofuro[2,3-b]indoles. Suárez-Castillo O. R., García-Velgara M., Morales-Ríos M. S., Joseph-Nathan P. DOI: 10.1139/v97-115
Abstract
3-Alkyl-2-hydroxyindolines, conveniently prepared from 2-hydroxyindolenines and a Grignard reagent, cyclize in the aprotic solvent tetrahydrofuran to afford tetrahydro-3-cyano-2-oxofuro[2,3-b]indoles, while in the protic solvent methanol the chemoselectivity changed to give dihydro-2-amino-3-carbomethoxyfuro[2,3-b]indoles. The steric effect of the alkyl group on the reactivity of 3-alkyl-2-hydroxyindolines is discussed for both processes. The ring transformation of tetrahydro-3-cyano-2-oxofuro[2,3-b]indoles into dihydro-2-amino-3-carbomethoxyfuro[2,3-b]indoles via ?-lactone imines is also discussed.
Role of lipid peroxidation in biliary obstruction in the rat
Conformational studies on indole alkaloids from Flustra foliacea by NMR and molecular modeling
Unimolecular rearrangements of ketene-O,O-acetals and fragmentations occurring in the gas phase
Synthesis of 6-bromo-2-arylindoles using 2-iodobenzoic acid as precursor
Stereochemical assignment of naturally occurring 2,3-epoxy-2-methylbutanoate esters
One-potsynthesis of conformationallyrestrictedspirooxindoles
Synthesis of Acetamido(indol-3-yl)propanol Derivatives
Trapping enols of esters and lactones with diazomethane
Cleavage of alkoxycarbonyl protecting groups from carbamates by t-BuNH2