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Paper | Regular issue | Vol 36, No. 12, 1993, pp.2723-2732
Published online, 1st January, 1970
DOI: 10.3987/COM-93-6491
Synthesis of Various Substituted Dibenzo[b,d]pyranones Including Amino Acid Derivatives by SRN1 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


An easy preparation of the title compounds involving a SRN1 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.