Issue 81, 2014

Reaction of α-amido sulfones with functionalized nitrocompounds: a new two-step synthesis of N-alkoxycarbonyl-2,5-disubstituted pyrroles

Abstract

Reaction of α-amido sulfones with nitro ketals promoted by KF on alumina provides the corresponding adducts which, upon treatment with p-toluenesulfonic acid, generate the corresponding N-alkoxycarbonyl-2,5-disubstituted pyrroles. The latter transformation involves a cascade process including ketal cleavage, ring closure and final aromatization by nitrous acid elimination.

Graphical abstract: Reaction of α-amido sulfones with functionalized nitrocompounds: a new two-step synthesis of N-alkoxycarbonyl-2,5-disubstituted pyrroles

Supplementary files

Article information

Article type
Communication
Submitted
04 Aug 2014
Accepted
05 Sep 2014
First published
08 Sep 2014
This article is Open Access
Creative Commons BY license

RSC Adv., 2014,4, 43258-43261

Author version available

Reaction of α-amido sulfones with functionalized nitrocompounds: a new two-step synthesis of N-alkoxycarbonyl-2,5-disubstituted pyrroles

R. Ballini, S. Gabrielli, A. Palmieri and M. Petrini, RSC Adv., 2014, 4, 43258 DOI: 10.1039/C4RA08112A

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

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