Issue 1, 2016

Facile synthesis of functionalized 6-cyano-2-oxa-7-azabicyclo[4.1.0]hept-3-en-1-yl acetates: a catalyst free approach to access the pyran fused 2-acetoxy-NH-aziridines

Abstract

Novel 6-cyano-2-oxa-7-azabicyclo[4.1.0]hept-3-en-1-yl acetate scaffolds were synthesized directly from 2-amino-3-cyano-4-H-pyrans as well as 2-amino-3-cyano-spiropyrans using iodobenzene diacetate (PIDA) as oxidant at room temperature in the absence of any catalyst. Essentially, the enamine fragment of the reactants reacts with PIDA, which makes this reaction a new way to synthesize pyran fused 2-acetoxy-NH-aziridines. These remarkably stable pyran fused 2-acetoxy-NH-aziridines can be used in SAR studies in pharmaceutical and medicinal chemistry. Ready availability of the starting materials, operational simplicity, absence of metal catalyst, mild reaction conditions, and simple workup procedure are the other significant features of this reaction.

Graphical abstract: Facile synthesis of functionalized 6-cyano-2-oxa-7-azabicyclo[4.1.0]hept-3-en-1-yl acetates: a catalyst free approach to access the pyran fused 2-acetoxy-NH-aziridines

Supplementary files

Article information

Article type
Paper
Submitted
19 Nov 2015
Accepted
11 Dec 2015
First published
16 Dec 2015

RSC Adv., 2016,6, 132-139

Author version available

Facile synthesis of functionalized 6-cyano-2-oxa-7-azabicyclo[4.1.0]hept-3-en-1-yl acetates: a catalyst free approach to access the pyran fused 2-acetoxy-NH-aziridines

P. Mukherjee and A. R. Das, RSC Adv., 2016, 6, 132 DOI: 10.1039/C5RA24510A

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