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Paper | Regular issue | Vol 78, No. 3, 2009, pp.679-690
Published online, 11th November, 2008
DOI: 10.3987/COM-08-11556
First Entry to [4+2] Cycloadditions Involving 5-Amino-2-furanmethanols

Raouf Medimagh, Sylvain Marque,* Damien Prim,* and Saber Chatti

*Institut Lavoisier de Versailles, UMR CNRS 8180, University of Versailles-Saint-Quentin-en-Yvelines, 78035 Versailles Cedex, France

Abstract

The preparation of new 5-amino-2-furanmethanols bearing various amino and primary or secondary alcohol groups is described. The structures of 5-amino-2-furanmethanols as dienes are consistent with 1H NMR data and cyloadditions of them allows the selective synthesis of tetrasubstituted aminobenzylic alcohols, amino phenols or lactones through Diels–Alder reactions.