Chemoselective direct amidation of fatty acids with furfurylamine without coupling reagents in reversed micellar microenvironment

Abstract

Furan heterocyclic compounds derived from renewable sources are popular versatile candidates for the production of multifunctional macromolecular materials. These compounds are also used as hydrophobilization monomers for reversible polyadducts or as versatile building blocks in Diels-Alder reactions. In the present study, an efficient approach to chemoselective acylation of furfurylamine with a series of non-preactivated monocarboxylic or dicarboxylic long-chain fatty acids and some of their functionalized derivatives has been achieved via catalytic direct amidation in reversed micellar medium. A convenient and environmentally friendly method has been developed for furfurylamides via a dehydrative coupling reaction. For this purpose, a new cationic Bronsted-type sulfonic acid catalyst containing a hexadecyl alkyl chain was synthesized and fully characterized. The present catalytic reaction produced the respective N-furfurylamides materials in good to excellent yields. This study also confirms that the direct amidation of carboxylic acids with selected amine compounds can be successfully catalyzed by Bronsted acids. Its simplicity and high atom economy are the main advantages of this method.A convenient chemoselective and direct amidation method to access to fatty acids-based furfurylamides as versatile building blocks in Diels-Alder reactions.image