Microwave-assisted synthesis of novel functionalized ketenimines and azadienes via a solvent-free reaction of isatoic anhydride, alkyl-Isocyanides and dialkyl acetylenedicarboxylates

Document Type: Research Article


Department of Chemistry, Shahr-e-Qods Branch, Islamic Azad University, Tehran, Iran


Ketenimines and azadienes are transient intermediates in organic chemistry especially in elimination-addition processes and in the formation of heterocyclic systems. These compounds play a considerable role as intermediates in synthesis of heterocyclic ring systems. In this present research synthesis of novel ketenimines and azadienes via multi component reactions (MCRs) based on alkyl-Isocyanides is reported. Following our ongoing interest in isocyanide-based MCRs, we reported stereo-selective reactions between 4H-3,1-benzoxazine-2,4(1H)-dione (isatoic anhydride) with dialkylacetylenedicarboxylates in the presence of alkyl isocyanides under solvent-free microwave conditions which leads to novel functionalized ketenimines and azadienes in a green route. The results show that the microwave-assisted leaching process has advantages over the conventional ones, with respect to energy-consumption, processing time and environmental protection.


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