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 prepared from acridine-4,5-diol ( 9) and phenazine-1,9-diol ( 10) with tetraethylene glycol di- p-tosylate ( 11) using potassium teri-butoxide as a base in THF. New optically pure dimethyl-substituted acridino- and phenazino-18-crown-6 li...

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Bibliographic Details
Published inTetrahedron Vol. 55; no. 5; pp. 1491 - 1504
Main Authors Huszthy, Péter, Samu, Erika, Vermes, Borbála, Mezey-Vándor, Gabriella, Nógrádi, Mihály, Bradshaw, Jerald S, Izatt, Reed M
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 29.01.1999
Elsevier
Subjects
Acridines
Chemistry
Chemistry, Organic
Crown ethers
Molecular recognition
Phenazines
Physical Sciences
Science & Technology
Molecular recognition
Acridines
Crown ethers
Phenazines
DIESTER
KINETIC DATA
ORGANIC AMMONIUM-SALTS
COMPLEXES
(S,S)-DIMETHYLPYRIDINO-18-CROWN-6
ENANTIOMERIC RECOGNITION
phenazines
crown ethers
acridines
CHIRAL PYRIDINO-18-CROWN-6 LIGANDS
PERCHLORATES
molecular recognition
MACROCYCLE INTERACTION
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Summary:Novel acridino- and phenazino-18-crown-6 ligands 5 and 6 were prepared from acridine-4,5-diol ( 9) and phenazine-1,9-diol ( 10) with tetraethylene glycol di- p-tosylate ( 11) using potassium teri-butoxide as a base in THF. New optically pure dimethyl-substituted acridino- and phenazino-18-crown-6 ligands (R,R)-7 and (R,R)-8 were also prepared by treating 9 and 10 with optically pure dimethyl-substituted tetraethylene glycol di- p-tosylate [(S,S)-18] . Molecular recognition studies on these novel ligands are underway. Graphic
ISSN:0040-4020
1464-5416
DOI:10.1016/S0040-4020(98)01128-4