Smiles Rearrangements in Ugi- and Passerini-Type Couplings:  New Multicomponent Access to O- and N-Arylamides

The use of Smiles rearrangement in Ugi- and Passerini-type couplings with electron-deficient phenols allows very straightforward multicomponent formation of O-aryl- and N-arylamides. Best yields were observed with the highly activated o- and p-nitrophenols, salicylic derivatives giving adducts in lo...

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Bibliographic Details
Published inJournal of organic chemistry Vol. 72; no. 11; pp. 4169 - 4180
Main Authors El Kaïm, Laurent, Gizolme, Marie, Grimaud, Laurence, Oble, Julie
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 25.05.2007
Amer Chemical Soc
Subjects
Amides - chemical synthesis
Catalysis
Chemistry
Chemistry, Organic
Cyclization
Heterocyclic Compounds - chemical synthesis
Molecular Structure
Nitrophenols - chemistry
Physical Sciences
Pyridines - chemistry
Science & Technology
Stereoisomerism
ALPHA-ADDITIONS
HETEROCYCLES
MIT ISONITRILEN
4-COMPONENT REACTION
ISOCYANIDES
CHEMISTRY
PRIMARY AMINES
CONDENSATION
ALDEHYDES
DERIVATIVES
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Summary:The use of Smiles rearrangement in Ugi- and Passerini-type couplings with electron-deficient phenols allows very straightforward multicomponent formation of O-aryl- and N-arylamides. Best yields were observed with the highly activated o- and p-nitrophenols, salicylic derivatives giving adducts in lower yields. The scope of these new reactions is further increased by the successful couplings of heterocyclic phenols such as hydroxypyridines and hydroxypyrimidines.
Bibliography:ark:/67375/TPS-JM3LSWXS-8
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ObjectType-Article-1
SourceType-Scholarly Journals-1
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content type line 23
ISSN:0022-3263
1520-6904
DOI:10.1021/jo070202e