Multicomponent Synthesis of 2-[Aryl(arylamino)methyl]furo[3,2-c]pyran-3,4-diones and Diastereoselective Furan Ring Opening to (Z)-3-[3-Aryl-3-(arylamino)acryloyl]-4-hydroxypyran-2-ones
Yamina Abdia, Baya Boutemeur-Kheddis*, Maamar Hamdi, Oualid Talhi, Khaldoun Bachari, Gilbert Kirsch, Artur M. S. Silva*
Jun 2016
Abstract : 

An efficient synthesis of novel 2-[aryl(arylamino)methyl]-6-methyl-4H-furo[3,2-c]pyran-3,4(2H)-diones is described by using a three-component reaction of α-bromodehydroaceticacid (α-Br-DHA) with anilines and benzaldehydes. Ammonium acetate is a suitable base to catalyse the diastereoselective tautomerism of the furo[3,2-c]pyran-3,4-diones into (Z)-3-[3-aryl-3-(arylamino)acryloyl]-4-hydroxy-6-methyl-2H-pyran-2-ones by opening the furan ring. These latter compounds were also obtained by a three-component reaction (α-Br-DHA, anilines, benzaldehydes) catalysed by ammonium acetate.


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