A rapid access to biaryl ether containing macrocycles by pairwise use of Ugi 4CR and intramolecular S(N)Ar-based cycloetherification

P Cristau; J P Vors; J Zhu

doi:10.1021/ol0168420

A rapid access to biaryl ether containing macrocycles by pairwise use of Ugi 4CR and intramolecular S(N)Ar-based cycloetherification

Org Lett. 2001 Dec 13;3(25):4079-82. doi: 10.1021/ol0168420.

Authors

P Cristau¹, J P Vors, J Zhu

Affiliation

¹ Institut de Chimie des Substances Naturelles, CNRS, 91198 Gif-sur-Yvette, France, and Aventis CropScience, 14-20 Rue Pierre Baizet, 69009 Lyon, France.

PMID: 11735589
DOI: 10.1021/ol0168420

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.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Ammonium Chloride / chemistry
Cyclization
Ethers / chemical synthesis*
Ethers / chemistry
Magnetic Resonance Spectroscopy
Molecular Structure
Solvents

Substances

Ethers
Solvents
Ammonium Chloride