Three-component synthesis of (E)-alpha,beta-unsaturated amides of the piperine family

Authors
Schobert, R Siegfried, S Gordon, GJ
Citation
R. Schobert et al., Three-component synthesis of (E)-alpha,beta-unsaturated amides of the piperine family, J CHEM S P1, (19), 2001, pp. 2393-2397
Citations number
30
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1
ISSN journal
14727781 → ACNP
Issue
19
Year of publication
2001
Pages
2393 - 2397
Database
ISI
SICI code
1472-7781(20011007):19<2393:TSO(AO>2.0.ZU;2-7
Abstract
Selective formation of (E)-alpha,beta -unsaturated amides by intermolecular three-component reaction between aldehydes, amines (1 degrees or 2 degrees ) and ketenylidenetriphenylphosphorane (Ph3P=C=C=O) is described. Natural a mides such as fagaramide and piperines could be prepared from immediately a vailable educts. The method is shown to be extendable to the preparation of thioesters from thiols and aldehydes.