Convenient syntheses and preliminary photophysical properties of novel 8-aminoquinoline appended diaza-18-crown-6 ligands

Novel 7,16-bis(8-amino-2-quinolinylmethyl)- and 7,16-bis(8-amino-7-quinolinylmethyl)-diaza-18-crown-6 ligands ( 12 and 16) have been synthesized by reductive amination of 8-(di- tert-butoxycarbonyl)amino-2-quinolinecarboxaldehyde (followed by removal of the Boc protecting groups) or 8-amino-7-quinol...

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Bibliographic Details
Published in:Tetrahedron 2001-09, Vol.57 (36), p.7623-7628
Main Authors: Xue, Guoping, Bradshaw, Jerald S, Dalley, N.Kent, Savage, Paul B, Krakowiak, Krzysztof E, Izatt, Reed M, Prodi, Luca, Montalti, Marco, Zaccheroni, Nelsi
Format: Article
Language:English
Subjects:
8-aminoquinoline
diazacrown ether
reductive amination
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Summary:Novel 7,16-bis(8-amino-2-quinolinylmethyl)- and 7,16-bis(8-amino-7-quinolinylmethyl)-diaza-18-crown-6 ligands ( 12 and 16) have been synthesized by reductive amination of 8-(di- tert-butoxycarbonyl)amino-2-quinolinecarboxaldehyde (followed by removal of the Boc protecting groups) or 8-amino-7-quinolinecarboxaldehyde with diaza-18-crown-6 using triacetoxyborohydride (NaBH(OAc) 3) as the reducing agent. The crystal structure of ligand 16 is also given. The absorption spectra of 12 and 16 are dominated by two intense bands at 250±5 and 238±1 nm which are blue shifted upon addition of alkaline earth and heavy metal ions in acetonitrile. In addition, intensities of the fluorescence bands of 12 and 16 are reduced in the presence of metal ions. Graphic
ISSN:0040-4020
1464-5416
DOI:10.1016/S0040-4020(01)00746-3