REGIOSELECTIVE SYNTHESIS OF 3-INDOLYL(ALKOXY)ACETATES

The regioselective synthesis of N-carbomethoxy-2-alkoxyindolenines and alpha-alkoxyindoles is reported. Bromination of indole 5 with NBS/AIBN/CCl(4) gave alpha-bromoindole 6 which after treatment with ROH/3 angstrom molecular Sieves afforded (Z-) and (E)-2-alkoxyindolenines 8a-d as the main products...

Full description

Saved in:
Bibliographic Details
Published inHeterocycles Vol. 81; no. 5; pp. 1169 - 1182
Main Authors Suarez-Castillo, Oscar R., Melendez-Rodriguez, Myriam, Cano-Escudero, Indira C., Luz De Ita-Gutierrez, Sandra, Sanchez-Zavala, Maricruz, Morales-Rios, Martha S., Joseph-Nathan, Pedro
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier 01.05.2010
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
OXIDATION
ALKYLATION
STEREOCONTROLLED TOTAL-SYNTHESIS
BISINDOLE ALKALOIDS
CARBONYL-COMPOUNDS
GLYOXYLATE
FRIEDEL-CRAFTS REACTION
ENANTIOSPECIFIC TOTAL-SYNTHESIS
DERIVATIVES
INDOLES
Online AccessGet more information

Cover

More Information
Summary:The regioselective synthesis of N-carbomethoxy-2-alkoxyindolenines and alpha-alkoxyindoles is reported. Bromination of indole 5 with NBS/AIBN/CCl(4) gave alpha-bromoindole 6 which after treatment with ROH/3 angstrom molecular Sieves afforded (Z-) and (E)-2-alkoxyindolenines 8a-d as the main products, together with minor amounts of alpha-alkoxyindoles 9a-d. The reversed regioselectivity was achieved in the absence of molecular Sieves to give alpha-alkoxyindoles 9a-d as the main products, while no traces of Z- or E-8a-d were detected.
ISSN:0385-5414
DOI:10.3987/COM-10-11904