ISOMERIZATION OF 4-AMINOBENZOFURANS TO 4-HYDROXYINDOLES

Authors
CHILIN A RODIGHIERO P GUIOTTO A
Citation
A. Chilin et al., ISOMERIZATION OF 4-AMINOBENZOFURANS TO 4-HYDROXYINDOLES, Synthesis, (3), 1998, pp. 309-312
Citations number
10
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Synthesis → ACNP
ISSN journal
00397881
Issue
3
Year of publication
1998
Pages
309 - 312
Database
ISI
SICI code
0039-7881(1998):3<309:IO4T4>2.0.ZU;2-0
Abstract
4-Amino-2-methylbenzofurans are quantitatively converted to 4-hydroxy- 2-methylindoles in acidic medium. The rearrangement mechanism involves the ring opening of the furan ring to produce an intermediate carboca tion, which undergoes ring closure to the indole system. Isomerization takes place only in the presence of a methyl substituent in 2 positio n.