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

被引：34

作者：

Xue, GP

Bradshaw, JS ^{[1
]}

Dalley, NK

Savage, PB

Krakowiak, KE

Izatt, RM

Prodi, L

Montalti, M

Zaccheroni, N

机构：

[1] Brigham Young Univ, Dept Chem & Biochem, Provo, UT 84602 USA

[2] IBC Adv Technol Inc, Amer Fork, UT 84003 USA

[3] Univ Bologna, Dipartimento Chim G Ciamician, I-40126 Bologna, Italy

来源：

TETRAHEDRON | 2001年 / 57卷 / 36期

关键词：

diazacrown ether; 8-aminoquinoline; reductive amination;

D O I：

10.1016/S0040-4020(01)00746-3

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Novel 7,16-bis(8-amino-2-quinohnylmethyl)- 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. (C) 2001 Elsevier Science Ltd. All rights reserved.

引用

页码：7623 / 7628

页数：6

共 17 条

[1] Reductive amination of aldehydes and ketones with sodium triacetoxyborohydride. Studies on direct and indirect reductive amination procedures [J].