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Paper | Regular issue | Vol 57, No. 3, 2002, pp.449-463
Published online, 1st January, 1970
DOI: 10.3987/COM-01-9408
Synthesis of New Atropisomers Derived from Methoxychloroacridine. Preparation of Enantiomerically Pure (aR)-(-)-2,2’-Dihydroxy-9,9’-biacridine

Anh Tuan Lormier, Gérard Boyer,* Robert Faure, and Jean Pierre Galy

*UMR 6009, Laboratoire de Valorisatin de la Chimie Fine, Case 552, Université Aix-Marseille III, Avenue Escadrille Normandie-Niemen, 13397 Marseille Cedex 20, France

Abstract

New biacridinyl atropisomers were obtained from symmetric ligand 2,2’-dihydroxy-9,9’-biacridine (4), prepared from 9-chloro-2-methoxyacridine. Alternative O-acylation and alkylation led to different polycycles and to a biacridinyl crown ether. The molecular structures of 2,2’-di(p-chlorobenzoyloxy)-9,9’-biacridinyl (5) and (9,9’-bisacridinyl)-2,2’-dihydroxy-bis-(camphanate) ester (13) were solved by X-Ray crystallography, showing a ‘scissor-like’ host conformation and guest inclusion of chloroform and acetonitrile. The determination of X-Ray structure of one diastereomer (13) allows to assign the absolute configuration of enantiomerically recovered (aR)-(-)-2,2’-dihydroxy-9,9’-biacridinyl.