An 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

Bartolo Gabriele; Pierluigi Plastina; Giuseppe Salerno; Raffaella Mancuso

doi:10.1055/s-2006-950360

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An 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

Bartolo Gabriele*^a, Pierluigi Plastina^b, Giuseppe Salerno^b, Raffaella Mancuso^b
^a Dipartimento di Scienze Farmaceutiche, Università della Calabria, 87036 Arcavacata di Rende (Cosenza), Italy
Fax: +39(0984)492044; e-Mail: b.gabriele@unical.it;
^b Dipartimento di Chimica, Università della Calabria, 87036 Arcavacata di Rende (Cosenza), Italy

Abstract

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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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References

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