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The synthesis of chromophore ended glycoles, part IV. Bis‐coumarin derivatives ended polyglycols
Author(s) -
Tuncer Hülya,
Erk ÇakL
Publication year - 2006
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570430501
Subject(s) - chemistry , coumarin , acetonitrile , chromophore , alkyl , trifluoromethyl , condensation , organic chemistry , mass spectrometry , proton nmr , medicinal chemistry , polymer chemistry , chromatography , physics , thermodynamics
The coumarin derivatives of bis‐resorcin ended polyglycols were prepared in two ways: Bis‐4‐alkyl‐7‐oxycoumarin ended mono and diethyleneglycols were prepared starting from bis(3‐hydroxyphenyl)glycols by coumarin condensation using relevant β‐ketoesters. Accordingly, 4‐methyl, 4‐trifluoromethyl, 4‐ n ‐propyl and 4‐phenyl derivatives of 7‐hydroxycoumarins were prepared in good yields. They were then converted to bis‐coumarin ended three and tetraethylenglycol derivatives by reacting with three and tetraethyleneglycols dichlorides in Na 2 CO 3 /DMF, respectively. The products were identified using IR, 1 H nmr and low resolution mass spectrometry. The Li + , Na + and Rb + metal/Ligand selectivities of cation binding behaviour of products in acetonitrile were studied with steady state fluorescence spectroscopy.