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■ Nucleophilic Aromatic Substitution of a Methoxy Group by an Alkylthio Group in the Case of 10-Substituted 2-Methoxy-9-thioacridinones

Djeridi Dhif, Jean-Pierre Galy,* Jacques Barbe, and José Elguero

*Laboratoire de Chimie Organique, Faculté de Pharmacie, Université de la Méditerranée, 27, Boulevard Jean Moulin, 13385 Marseille Cedex 05, France

Abstract

The synthesis and nmr study (¹H and ¹³C) of eleven acridine derivatives are reported. ¹³C chemical shifts are very sensitive to the oxygen or sulfur nature of the substituents at positions 2 (alkoxy vs thioalkoxy) and 9 (acridinones vs thioacridinones). The rather unusual replacement of an alkoxy group by a thioalkoxy group in thioacridinones, when treated by alkyl mercaptans in the presence of aluminium chloride, is described.