Back to Search Start Over

An acid-promoted novel skeletal rearrangement initiated by intramolecular ipso-Friedel-Crafts-type addition to 3-alkylidene indolenium cations.

Authors :
Yokosaka T
Nemoto T
Hamada Y
Source :
Chemical communications (Cambridge, England) [Chem Commun (Camb)] 2012 Jun 04; Vol. 48 (44), pp. 5431-3. Date of Electronic Publication: 2012 Apr 27.
Publication Year :
2012

Abstract

An acid-promoted novel skeletal rearrangement is described. Using trifluoroacetic acid as the acid promoter, an intramolecular ipso-Friedel-Crafts-type addition of phenols to 3-alkylidene indolenium cations, formation of iminium cations through rearomatization of the spirocyclohexadienone units, and intramolecular Pictet-Spengler reaction proceeded sequentially, producing tricyclic indole derivatives.

Details

Language :
English
ISSN :
1364-548X
Volume :
48
Issue :
44
Database :
MEDLINE
Journal :
Chemical communications (Cambridge, England)
Publication Type :
Academic Journal
Accession number :
22543858
Full Text :
https://doi.org/10.1039/c2cc31699d