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Synthesis of 2,4,5-trisubstituted oxazoles through tin(iv) chloride-mediated reaction of trans-2-aryl-3-nitro-cyclopropane-1,1-dicarboxylates with nitriles†
Thangavel Selvi,Kannupal Srinivasan
Chemical Communications Pub Date : 07/24/2014 00:00:00 , DOI:10.1039/C4CC04764H
Abstract

trans-2-Aryl-3-nitro-cyclopropane-1,1-dicarboxylates when reacted with nitriles in the presence of tin(IV) chloride afford 2,4,5-trisubstituted oxazoles in good to excellent yields. The reactions take place through in situ generation of aroylmethylidene malonates from the cyclopropanes, followed by conjugate addition of nitriles to the malonates to form nitrilium ion intermediates and subsequent cyclisation.

Graphical abstract: Synthesis of 2,4,5-trisubstituted oxazoles through tin(iv) chloride-mediated reaction of trans-2-aryl-3-nitro-cyclopropane-1,1-dicarboxylates with nitriles
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