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.

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

GABRIELE, Bartolo;PLASTINA, Pierluigi;MANCUSO R.
2006

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.
Carbonylation; Palladium; Furans; heterocycles
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/20.500.11770/124895
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