A Rapid Access to Biaryl Ether Containing Macrocycles by Pairwise Use of Ugi 4CR and Intramolecular SNAr-Based Cycloetherification
2001
Abstract
An Ugi reaction promoted by ammonium chloride in aprotic solvent is documented here for the first time. From readily accessible starting materials, macrocycles with an endo aryl-aryl ether bond are synthesized in only two steps, Ugi four-component reaction (Ugi 4CR) and an intramol. SNAr reaction. The nitro group serves as an activator for the macrocyclization and provides a handle for the introduction of functional group diversity. For example, dipeptide amide I was obtained in an Ugi 4CR from isonitrile II, PhCHO, PhCH2NH2 and 3-hydroxyphenylacetic acid in the presence of NH4+Cl- in toluene at 0 Deg for 20 h. Cycloetherification of I took place in the presence of K2CO3 in DMF for 3 h to give macrocycle III in 80% yield. [on SciFinder (R)]
Details
Title
A Rapid Access to Biaryl Ether Containing Macrocycles by Pairwise Use of Ugi 4CR and Intramolecular SNAr-Based Cycloetherification
Author(s)
Cristau, Pierre ; Vors, Jean-Pierre ; Zhu, Jieping
Published in
Organic Letters
Volume
3
Issue
25
Pages
4079-4082
Date
2001
ISSN
1523-7060
Keywords
Addition reaction (Ugi; prepn. of biaryl ether-contg. macrocycles by Ugi four component reaction and intramol. SNAr-based cycloetherification); Ethers Role: SPN (Synthetic preparation); PREP (Preparation) (arom.; macrocyclic; prepn. of biaryl ether-contg. macrocycles by Ugi four component reaction and intramol. SNAr-based cycloetherification); Macrocyclic compounds Role: SPN (Synthetic preparation); PREP (Preparation) (biaryl ethers; prepn. of biaryl ether-contg. macrocycles by Ugi four component reaction and intramol. SNAr-based cycloetherification); Macrocyclization (etherification; prepn. of biaryl ether-contg. macrocycles by Ugi four component reaction and intramol. SNAr-based cycloetherification); Etherification (macrocyclization; prepn. of biaryl ether-contg. macrocycles by Ugi four component reaction and intramol. SNAr-based cycloetherification); macrocycle biaryl ether prepn Ugi 4CR SNAr cycloetherification; Ugi four component reaction ammonium chloride reagent aprotic solvent; macrocyclization SNAr based etherification
Note
CAN 136:118732
34-3
Amino Acids, Peptides, and Proteins
Institut de Chimie des Substances Naturelles,CNRS,Gif-sur-Yvette,Fr.
Journal
written in English.
75-31-0 (Isopropylamine); 78-84-2 (Iso-butyraldehyde); 100-46-9 (Benzylamine); 100-52-7 (Benzaldehyde); 104-53-0 (Benzenepropanal); 104-94-9 (p-Methoxyaniline); 109-73-9 (n-Butylamine); 111-71-7 (n-Heptanal); 120-20-7; 459-57-4 (4-Fluorobenzaldehyde); 621-37-4; 621-54-5; 3173-56-6 (Benzyl isocyanate); 15017-52-4; 58885-60-2 Role: RCT (Reactant), RACT (Reactant or reagent) (prepn. of biaryl ether-contg. macrocycles by Ugi four component reaction and intramol. SNAr-based cycloetherification); 20274-69-5P; 42564-51-2P; 389634-80-4P; 389634-81-5P; 389634-82-6P; 389634-83-7P; 389634-84-8P; 389634-85-9P; 389634-86-0P; 389634-87-1P; 389634-88-2P; 389634-89-3P; 389634-97-3P; 389634-98-4P; 389634-99-5P; 389635-00-1P; 389635-01-2P; 389635-02-3P; 389635-04-5P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. of biaryl ether-contg. macrocycles by Ugi four component reaction and intramol. SNAr-based cycloetherification); 389635-03-4P; 389635-05-6P; 389635-06-7P; 389829-05-4P; 389829-08-7P; 389829-10-1P; 389829-13-4P; 389829-15-6P; 389829-18-9P; 389829-21-4P; 389829-24-7P; 390360-55-1P; 390360-57-3P; 390360-59-5P; 390360-61-9P; 390360-63-1P; 390360-65-3P; 390360-67-5P; 390360-69-7P; 390360-71-1P; 390360-73-3P; 390360-75-5P; 390360-77-7P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. of biaryl ether-contg. macrocycles by Ugi four component reaction and intramol. SNAr-based cycloetherification)
34-3
Amino Acids, Peptides, and Proteins
Institut de Chimie des Substances Naturelles,CNRS,Gif-sur-Yvette,Fr.
Journal
written in English.
75-31-0 (Isopropylamine); 78-84-2 (Iso-butyraldehyde); 100-46-9 (Benzylamine); 100-52-7 (Benzaldehyde); 104-53-0 (Benzenepropanal); 104-94-9 (p-Methoxyaniline); 109-73-9 (n-Butylamine); 111-71-7 (n-Heptanal); 120-20-7; 459-57-4 (4-Fluorobenzaldehyde); 621-37-4; 621-54-5; 3173-56-6 (Benzyl isocyanate); 15017-52-4; 58885-60-2 Role: RCT (Reactant), RACT (Reactant or reagent) (prepn. of biaryl ether-contg. macrocycles by Ugi four component reaction and intramol. SNAr-based cycloetherification); 20274-69-5P; 42564-51-2P; 389634-80-4P; 389634-81-5P; 389634-82-6P; 389634-83-7P; 389634-84-8P; 389634-85-9P; 389634-86-0P; 389634-87-1P; 389634-88-2P; 389634-89-3P; 389634-97-3P; 389634-98-4P; 389634-99-5P; 389635-00-1P; 389635-01-2P; 389635-02-3P; 389635-04-5P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. of biaryl ether-contg. macrocycles by Ugi four component reaction and intramol. SNAr-based cycloetherification); 389635-03-4P; 389635-05-6P; 389635-06-7P; 389829-05-4P; 389829-08-7P; 389829-10-1P; 389829-13-4P; 389829-15-6P; 389829-18-9P; 389829-21-4P; 389829-24-7P; 390360-55-1P; 390360-57-3P; 390360-59-5P; 390360-61-9P; 390360-63-1P; 390360-65-3P; 390360-67-5P; 390360-69-7P; 390360-71-1P; 390360-73-3P; 390360-75-5P; 390360-77-7P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. of biaryl ether-contg. macrocycles by Ugi four component reaction and intramol. SNAr-based cycloetherification)
Laboratories
LSPN
Record Appears in
Scientific production and competences > SB - School of Basic Sciences > ISIC - Institute of Chemical Sciences and Engineering > LSPN - Laboratory of synthesis and natural products
Peer-reviewed publications
Work outside EPFL
Journal Articles
Published
Peer-reviewed publications
Work outside EPFL
Journal Articles
Published
Record creation date
2010-11-25