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Solvent-Free Synthesis of Enamines from Alkyl Esters of Propiolic or But-2-yne Dicarboxylic Acid in a Ball Mill

Rico Thorwirth, Achim Stolle*

*Institute for Technical Chemistry and Environmental Chemistry (ITUC), Friedrich-Schiller University Jena, Lessingstr. 12, 07743 Jena, Germany, Email: Achim.Stolleuni-jena.de

R. Thorwirth, A. Stolle, Synlett, 2011, 2200-2202.

DOI: 10.1055/s-0030-1261179


Abstract

The use of a planetary ball mill enables a solvent-free method for the addition of amines to dialkylacetylendicarboxylates or alkylpropiolates. Conversion of educts was quantitative within five minutes without use of any catalyst or base. Beside the E-/Z-isomers, no side products were formed.

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Key Words

addition, amines, alkynes, β-enamino esters, green chemistry, mechanochemistry


ID: J60-Y2011-2740