Issue 15, 2003
From the journal:

Organic & Biomolecular Chemistry

Spiroheterocycles from reaction of nitrones with methylene-γ-butyrolactones and some of their rearrangements

Christophe Roussel,†a   Rachid Fihi,b   Kabula Ciamala,*a   Joël Vebrel,a   Touria Zairc  and  Claude Riched  

* Corresponding authors

a Laboratoire de Chimie des Matériaux et Interfaces, UFR Sciences et Techniques, 16 Route de Gray, F-25030 BESANCON Cedex, France

b Laboratoire des Substances Naturelles-Synthèse et Dynamique Moléculaire, Faculté des Sciences et des Techniques, BP 509, ERRACHIDIA-Maroc

c Laboratoire de Chimie Organique Appliquée, Faculté des Sciences, BP 4010, Beni M'hamed MEKNES-Maroc

d Laboratoire de Cristallochimie, Institut de Chimie des Substances Naturelles-CNRS, Avenue de la Terrasse, F-91198 GIF SUR YVETTE Cedex, France

Abstract

Cycloaddition of nitrones 1 with methylene-γ-butyrolactones 2, 3 and 4 afforded spiroadducts 5, 6 and 7 with high selectivity. Mixtures of diastereoisomers were usually obtained, whose structures were established by 1H and 13C NMR spectroscopies or X-ray crystallography. Treatment of spiroadducts in acidic and alkaline media led to different, unexpected and novel rearrangements.

Graphical abstract: Spiroheterocycles from reaction of nitrones with methylene-γ-butyrolactones and some of their rearrangements

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Article information

DOI
https://doi.org/10.1039/B300628J
Article type
Paper
Submitted
22 Jan 2003
Accepted
06 Jun 2003
First published
30 Jun 2003

Org. Biomol. Chem., 2003,1, 2689-2698

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Spiroheterocycles from reaction of nitrones with methylene-γ-butyrolactones and some of their rearrangements

C. Roussel, R. Fihi, K. Ciamala, J. Vebrel, T. Zair and C. Riche, Org. Biomol. Chem., 2003, 1, 2689 DOI: 10.1039/B300628J

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