Producción Científica Profesorado

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.



Producto de Investigación




Artículos relacionados

Conformational studies on indole alkaloids from Flustra foliacea by NMR and molecular modeling

Stereochemical assignment of naturally occurring 2,3-epoxy-2-methylbutanoate esters

The absoluteconfiguration of cuauhtemone and related compounds

Unimolecular rearrangements of ketene-O,O-acetals and fragmentations occurring in the gas phase

Configuration, stereodynamics and crystal structure of 3-substituted-2-oxofuro[2,3-b]indoles

Synthesis of 6-bromo-2-arylindoles using 2-iodobenzoic acid as precursor

Aromatic Bromination versus Oxidation of Indolylmalonates by Bromine

First Total Synthesis of ()-Flustraminol B

13C NMR and crystallographic evidence of push-pull effects in furoindolic ?-enamino esters

Synthesis of Indolylindolines Mediated by tert-BuNH2