Issue 44, 2012
From the journal:

Chemical Communications

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

Takuya Yokosaka,a   Tetsuhiro Nemotoa  and  Yasumasa Hamada*a  

* Corresponding authors

a Graduate School of Pharmaceutical Sciences, Chiba University, 1-8-1, Inohana, Chuo-ku, Chiba 260-8675, Japan
E-mail: hamada@p.chiba-u.ac.jp
Fax: +81-43-226-2920
Tel: +81-43-226-2920

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.

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

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Article information

DOI
https://doi.org/10.1039/C2CC31699D
Article type
Communication
Submitted
07 Mar 2012
Accepted
10 Apr 2012
First published
11 Apr 2012

Chem. Commun., 2012,48, 5431-5433

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

T. Yokosaka, T. Nemoto and Y. Hamada, Chem. Commun., 2012, 48, 5431 DOI: 10.1039/C2CC31699D

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