Synthesis of 2-(alkylamino)-5-{alkyl[(2-oxo-2H-chromen-3-yl)carbonyl]amino}-3,4-furandicarboxylates using a multi-component reaction in water

• DOI: 10.1016/j.tet.2010.09.032
• Publication Date: 2010-09-18T08:27:29Z
• Authors: Mehdi Adib; Ehsan Sheikhi; Azadeh Kavoosi; Hamid Reza Bijanz...
• Keywords: 01 natural sciences; 0104 chemical sciences

Abstract A simple synthesis of 2-(alkylamino)-5-{alkyl[(2-oxo-2H-chromen-3-yl)carbonyl]amino}-3,4-furandicarboxylates via a one-pot multi-component reaction is described. The reactive 1:1 zwitterionic intermediate generated from the addition of isocyanides to dialkyl acetylenedicarboxylates was trapped at room temperature by coumarin-3-carboxylic acids prepared in situ from a 2-hydroxy aromatic aldehyde and Meldrum’s acid to afford the title compounds in good to excellent yields.