Synthesis of novel acridino- and phenazino-18-crown-6 ligands and their optically pure dimethyl-substituted analogues for molecular recognition studies

Novel acridino- and phenazino-18-crown-6 ligands 5 and 6 were I,prepared fr om acridine-4.5-diol (9) and phenazine-1,9-diol (10) with tetraethylene gly col di-p-tosylate (11) using potassium tert-butoxide as a bar in THF. New o ptically pure dimethyl-substituted acridino- and phenazine-18-crown-6 ligan ds (R,R)-7 and (R,R)-8 were also prepared by treating 9 and 10 with optical ly pure dimethyl-substituted tetraethylene glycol di-p-tosylate [(S,S)-18], Molecular recognition studies on these novel ligands are underway. (C) 199 9 Elsevier Science Ltd. All rights reserved.