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Phenol Ugi–Smiles Systems: Strategies for the Multicomponent N ‐ Arylation of Primary Amines with Isocyanides, Aldehydes, and Phenols
Author(s) -
El Kaïm Laurent,
Grimaud Laurence,
Oble Julie
Publication year - 2005
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200502636
Subject(s) - chemistry , isocyanide , carboxylic acid , ugi reaction , nucleophile , adduct , aryl , organic chemistry , combinatorial chemistry , medicinal chemistry , alkyl , catalysis
A Smiles rearrangement is the key step in the efficient coupling of primary amines with isocyanides, carbonyl compounds, and electron‐deficient substituted phenols to form N ‐aryl amines (see picture). The presence of a nitro or ester group on the resulting adduct allows applications in heterocyclic synthesis.
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