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■ Synthesis of Various Substituted Dibenzo[b,d]pyranones Including Amino Acid Derivatives by S_RN1 Methodology

Rene Beugelmans, Michèle Bois-Choussy,* Jacqueline Chastanet, Martine Le Gleuher, and Jieping Zhu

*Institut des Chimie des Substances Naturelles, C.N.R.S., Avenue de la Terrasse, Bat. 27, 91198 Gif-sur-Yvette Cedex, France

Abstract

An easy preparation of the title compounds involving a S_RN1 ortho-arylation of phenolates by o-bromobenzonitrile followed by SiO₂-catalysed lactonisation is described. Activated or not activated phenols are efficient. Access to benzonaphthopyranones is exemplified by the reactions with 2-naphtholate. Reactions with chiral p-hydroxyphenylamino acid derivatives are also reported.