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Issue 74, 2014
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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

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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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Article information


Submitted
23 Jun 2014
Accepted
23 Jul 2014
First published
24 Jul 2014

Chem. Commun., 2014,50, 10845-10848
Article type
Communication

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

T. Selvi and K. Srinivasan, Chem. Commun., 2014, 50, 10845
DOI: 10.1039/C4CC04764H

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