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A rapid access to biaryl ether containing macrocycles by pairwise use of Ugi 4CR and intramolecular S(N)Ar-based
1Institut de Chimie des Substances Naturelles, CNRS, 91198 Gif-sur-Yvette, France, and Aventis CropScience, 14-20 Rue Pierre Baizet, 69009 Lyon, France.
Organic Letters
|December 12, 2001
Abstract:
[reaction: see text] From readily accessible starting materials, macrocycles with an endo aryl-aryl ether bond are synthesized in only two operations by combination of the Ugi four-component reaction and an intramolecular S(N)Ar reaction. The nitro group serves as an activator for the macrocyclization and provides a handle for the introduction of functional group diversity. A Ugi reaction promoted by ammonium chloride in aprotic solvent is documented for the first time.