Phenol Ugi-Smiles Systems: Strategies for the Multicomponent N-Arylation of Primary Amines with Isocyanides, Aldehydes, and Phenols

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...

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Published inAngewandte Chemie (International ed.) Vol. 44; no. 48; pp. 7961 - 7964
Main Authors El Kaïm, Laurent, Grimaud, Laurence, Oble, Julie
Format Journal Article
LanguageEnglish
Published Weinheim WILEY-VCH Verlag 09.12.2005
WILEY‐VCH Verlag
Wiley
Subjects
amines
arylation
Chemistry
Chemistry, Multidisciplinary
multicomponent reaction
phenols
Physical Sciences
rearrangement
Science & Technology
phenols
amines
ISONITRILE
CHEMISTRY
multicomponent reaction
rearrangement
arylation
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Summary: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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ISSN:1433-7851
1521-3773
DOI:10.1002/anie.200502636