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Paper | Regular issue | Vol 31, No. 6, 1990, pp.1059-1065
Published online, 1st January, 1970
DOI: 10.3987/COM-90-5337
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


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.