Rearrangement of Aryl Geranyl Ethers

Abstract

This article describes the thermal rearrangement reactions of aryl geranyl ethers. These reactions depend on the structure of the aryl moiety of the substrate and the reaction conditions used. The naphthyl ethers underwent a [1,3]-alkyl shift, followed by acid-catalyzed intramolecular cyclization. The microwave-assisted rearrangement of isoquinolinyl ether showed a pattern of an abnormal Claisen rearrangement. The multi step rearrangement of the quinolyl ether afforded a spiro compound. These new reactions were used to synthesize novel heterocyclic compounds.

GRAPHICAL ABSTRACT

Keywords:

• Benzo[h]chromene
• benzo[a]xanthene
• furo[3,2-f]isoquinoline
• furo[3,2-h]quinoline
• microwave-assisted synthesis
• rearrangement