FACILE SYNTHESIS OF 6-HYDROXYINDOLE AND 6-METHOXYINDOLE VIA REGIOSELECTIVE FRIEDEL-CRAFTS ACYLATION AND BAEYER-VILLIGER OXIDATION

Authors
TERANISHI K NAKATSUKA S GOTO T
Citation
K. Teranishi et al., FACILE SYNTHESIS OF 6-HYDROXYINDOLE AND 6-METHOXYINDOLE VIA REGIOSELECTIVE FRIEDEL-CRAFTS ACYLATION AND BAEYER-VILLIGER OXIDATION, Synthesis, (10), 1994, pp. 1018-1020
Citations number
20
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Synthesis → ACNP
ISSN journal
00397881
Issue
10
Year of publication
1994
Pages
1018 - 1020
Database
ISI
SICI code
0039-7881(1994):10<1018:FSO6A6>2.0.ZU;2-5
Abstract
A facile synthesis of 6-hydroxyindole and 6-methoxyindole starting fro m indole is described. Regioselective chloroacetylation of 1-pivaloyli ndole followed by Baeyer-Villiger oxidation offers introduction of an oxygen function into the 6-position of the indole ring. Deacylation of 6-chloroacetyl-1-pivaloylindole gives 6-hydroxyindole which is conver ted to 6-methoxyindole by methylation. The overall yield of 6-hydroxyi ndole and 6-methoxyindole from indole is 54 and 37%, respectively.