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Synthesis 2006(24): 4247-4251
DOI: 10.1055/s-2006-950360
DOI: 10.1055/s-2006-950360
PAPER
© Georg Thieme Verlag Stuttgart · New YorkAn Easy and Convenient Synthesis of 2-Furan-2-ylacetamides by Sequential Palladium-Catalyzed Oxidative Aminocarbonylation of (Z)-2-En-4-yn-1-ols/Conjugate Addition/Aromatization
Further Information
Received
31 July 2006
Publication Date:
02 November 2006 (online)
Publication History
Publication Date:
02 November 2006 (online)
Abstract
A simple and convenient synthesis of 2-furan-2-ylacetamides 4 starting from readily available (Z)-2-en-4-yn-1-ols 1 is reported. The method is based on a PdI2-catalyzed oxidative aminocarbonylation of the triple bond of 1 to give the corresponding 2-ynamide intermediates 2, which undergo intramolecular conjugate addition to give 2-(5H-furan-2-ylidene)acetamide derivatives 3. Spontaneous or one-pot acid-promoted aromatization of 3 eventually leads to the final furanacetamide derivatives 4.
Key words
aminocarbonylation - furans - 2-furan-2-ylacetamides - palladium
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