A rapid access to biaryl ether containing macrocycles by pairwise use of Ugi 4CR and intramolecular S(N)Ar-based cycloetherification.
[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.
Cristau
P
P
Institut de Chimie des Substances Naturelles, CNRS, 91198 Gif-sur-Yvette, France, and Aventis CropScience, 14-20 Rue Pierre Baizet, 69009 Lyon, France.
Vors
J P
JP
Zhu
J
J
D000643:Ammonium Chloride / Q000737:chemistry; D003500:Cyclization; D004987:Ethers / Q000138:chemical synthesis* / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D012997:Solvents
D004987:Ethers; D012997:Solvents; D000643:Ammonium Chloride