Lewis acid-catalyzed formation of Ugi four-component reaction product from Passerini three-component reaction system without an added amine

In the presence of a Lewis acid the phenol-Passerini three-component reaction (phenol-P-3CR) system is found to deliver a product of the phenol-Ugi four-component reaction (phenol-U-4CR). It is the first demonstration of an isocyanide as an amine equivalent in isocyanide-based multicomponent reactio...

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Bibliographic Details
Published in:Tetrahedron 2007-12, Vol.63 (52), p.12866-12876
Main Authors: Dai, Wei-Min, Li, Huoming
Format: Article
Language:English
Subjects:
Lewis acid
P-3CR
Phenols
Smiles rearrangement
U-4CR
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Summary:In the presence of a Lewis acid the phenol-Passerini three-component reaction (phenol-P-3CR) system is found to deliver a product of the phenol-Ugi four-component reaction (phenol-U-4CR). It is the first demonstration of an isocyanide as an amine equivalent in isocyanide-based multicomponent reactions (IMCRs). In general, by using Ti(O- i-Pr) 4 in MeOH both phenol-U-4CR and U-4CR products are synthesized from an aromatic aldehyde, a phenolic or carboxylic acid, and an isocyanide. Moreover, by using MeCN as the solvent, the phenol-P-3CR products can be obtained in good yields without contamination of the phenol-U-4CR products. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2007.10.050