Issue 41, 2006
From the journal:

Chemical Communications

Ring opening and ring closure in an indolizine structure activated through SNAr coupling with superelectrophilic 4,6-dinitrobenzofuroxan, an unusual intramolecular oxygen transfer from a N-oxide functionality

Sergey Kurbatov,a   Artem Tatarov,a   Vladimir Minkin,a   Régis Goumontb  and  François Terrier*b  

* Corresponding authors

a Department of Chemistry, Rostov State University, 7, Zorge St., 344090 Rostov-on-Don, Russia

b Institut Lavoisier, UMR 8180, University of Versailles, 45, Avenue des Etats-Unis, 78035 Versailles Cedex, France
E-mail: terrier@chimie.uvsq.fr

Abstract

Coupling of superelectrophilic 4,6-dinitrobenzofuroxan with a π-excessive indolizine structure affords a strongly dipolar substitution product which undergoes a facile but unusual rearrangement induced by an intramolecular oxygen atom transfer from the N-oxide functionality of the DNBF moiety.

Graphical abstract: Ring opening and ring closure in an indolizine structure activated through SNAr coupling with superelectrophilic 4,6-dinitrobenzofuroxan, an unusual intramolecular oxygen transfer from a N-oxide functionality

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Article information

DOI
https://doi.org/10.1039/B608350A
Article type
Communication
Submitted
13 Jun 2006
Accepted
24 Jul 2006
First published
01 Sep 2006

Chem. Commun., 2006, 4279-4281

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Ring opening and ring closure in an indolizine structure activated through SNAr coupling with superelectrophilic 4,6-dinitrobenzofuroxan, an unusual intramolecular oxygen transfer from a N-oxide functionality

S. Kurbatov, A. Tatarov, V. Minkin, R. Goumont and F. Terrier, Chem. Commun., 2006, 4279 DOI: 10.1039/B608350A

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