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Issue 18, 2006
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New ortho-quinone methide formation: application to three-component coupling of isocyanides, aldehydes and phenols

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Abstract

Herein, we wish to report a new three-component formation of heterocyclic scaffolds based on a one-pot process from simple phenols. The key step of this procedure involves an ortho-quinone methide formation from Mannich adducts under alkylative conditions. The transient o-quinone methide has been trapped in situ with indole and diketone using lithium perchlorate as catalyst. The interest of this procedure has been furthermore demonstrated by a new three-component aminobenzofuran formation from phenols, aldehydes and isocyanides.

Graphical abstract: New ortho-quinone methide formation: application to three-component coupling of isocyanides, aldehydes and phenols

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Article information


Submitted
17 Jul 2006
Accepted
27 Jul 2006
First published
08 Aug 2006

Org. Biomol. Chem., 2006,4, 3410-3413
Article type
Communication

New ortho-quinone methide formation: application to three-component coupling of isocyanides, aldehydes and phenols

L. El Kaïm, L. Grimaud and J. Oble, Org. Biomol. Chem., 2006, 4, 3410
DOI: 10.1039/B610229H

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