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Issue 84, 2014

Synthesis of nitrogen-containing fused-polycyclic compounds from tyramine derivatives using phenol dearomatization and cascade cyclization

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Abstract

We developed a novel method of synthesizing nitrogen-containing fused-polycyclic compounds using tyramine derivatives as substrates. The method is based on the dearomatization of phenols via an intramolecular ipso-Friedel–Crafts allenylation and sequential bond-forming–cleavage reactions initiated by the construction of an indole skeleton. Structurally diverse fused-heterocycles were produced in reaction sequences requiring only a few steps.

Graphical abstract: Synthesis of nitrogen-containing fused-polycyclic compounds from tyramine derivatives using phenol dearomatization and cascade cyclization

Supplementary files

Article information


Submitted
24 Jun 2014
Accepted
05 Sep 2014
First published
05 Sep 2014

Chem. Commun., 2014,50, 12775-12778
Article type
Communication

Synthesis of nitrogen-containing fused-polycyclic compounds from tyramine derivatives using phenol dearomatization and cascade cyclization

T. Yokosaka, T. Nemoto, H. Nakayama, N. Shiga and Y. Hamada, Chem. Commun., 2014, 50, 12775 DOI: 10.1039/C4CC04809A

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