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
One-potsynthesis of conformationallyrestrictedspirooxindoles
Synthesis of Acetamido(indol-3-yl)propanol Derivatives
Role of lipid peroxidation in biliary obstruction in the rat
Synthesis of Bromoindole Alkaloids from Laurencia brongniartii
Conformational studies on indole alkaloids from Flustra foliacea by NMR and molecular modeling
Aromatic Bromination versus Oxidation of Indolylmalonates by Bromine
Cleavage of alkoxycarbonyl protecting groups from carbamates by t-BuNH2
Total Syntheses of Five Indole Alkaloids from the Marine Bryozoan Flustra foliacea