Regioselective Synthesis of 3-Indolyl(alkoxy)acetates
Suárez Castillo, Oscar Rodolfo
2010
Suárez-Castillo O. R., Meléndez-Rodríguez M., Cano-Escudero Indira C., De Ita-Gutiérrez Sandra Luz, Sánchez-Zavala M., Morales-Ríos M. S. y Joseph-Nathan P., Regioselective Synthesis of 3-indolyl(alcoxy)acetates Heterocycles, 81, 1169, (2010).ISSN: 0385-5414
Abstract
The regioselective synthesis of N-carbomethoxy-2-alkoxyindolenines and ?-alkoxyindoles is reported. Bromination of indole 5 with NBS/AIBN/CCl4 gave ?-bromoindole 6 which after treatment with ROH/3Å molecular Sieves afforded (Z-) and (E)-2-alkoxyindolenines 8a-d as the main products, together with minor amounts of ?-alkoxyindoles 9a-d. The reversed regioselectivity was achieved in the absence of molecular Sieves to give ?-alkoxyindoles 9a-d as the main products, while no traces of Z- or E-8a-d were detected.
Artículos relacionados
Aromatic Bromination versus Oxidation of Indolylmalonates by Bromine
Conformational studies on indole alkaloids from Flustra foliacea by NMR and molecular modeling
Transesterifications mediated by t-BuNH2
Configuration, stereodynamics and crystal structure of 3-substituted-2-oxofuro[2,3-b]indoles
Synthesis of Acetamido(indol-3-yl)propanol Derivatives
Unimolecular rearrangements of ketene-O,O-acetals and fragmentations occurring in the gas phase
Stereochemical assignment of naturally occurring 2,3-epoxy-2-methylbutanoate esters
Cleavage of alkoxycarbonyl protecting groups from carbamates by t-BuNH2