Synthesis of 4-amino substituted 1,8-naphthalimide derivatives using palladium-mediated amination

被引:16
作者
Fleming, Cassandra L. [1 ]
Ashton, Trent D. [1 ]
Pfeffer, Frederick M. [1 ]
机构
[1] Deakin Univ, Sch Life & Environm Sci, Res Ctr Chem & Biotechnol, Waurn Ponds, Vic 3216, Australia
基金
澳大利亚研究理事会;
关键词
Synthesis; 4-Aminonaphthalimide; Buchwald-Hartwig; Amination; Naphthalimide; Palladium; BUCHWALD-HARTWIG AMINATION; APPENDED NAPHTHALIMIDE; DYES; RECEPTORS; ANHYDRIDE; BINDING; DESIGN;
D O I
10.1016/j.dyepig.2014.05.006
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
Successful amination of 4-bromo-1,8-naphthalimides with 'lengthy' imide N-functionality has been achieved using a general palladium mediated approach (conventional thermal protocols were suboptimal). Only readily available Pd/ligand combinations were considered and the resulting Buchwald-Hartwig procedure using Pd-2(dba)(3), Xantphos and Cs2CO3 is high yielding, relatively mild (40-80 degrees C, 24 h, yields 50-90%), requires only a modest excess of amine (3.0 equiv) and works equally well with other imide N-substituents. As such, the protocol complements existing methods but is superior for more complex substrates. Herein we compare this Pd mediated approach to the methods most commonly used and further demonstrate its utility by synthesising a number of new, highly fluorescent, 4-aminonaphthalimides. (C) 2014 Elsevier Ltd. All rights reserved.
引用
收藏
页码:135 / 143
页数:9
相关论文
共 46 条
[1]   THE UV-VISIBLE ABSORPTION AND FLUORESCENCE OF SOME SUBSTITUTED 1,8-NAPHTHALIMIDES AND NAPHTHALIC ANHYDRIDES [J].
ALEXIOU, MS ;
TYCHOPOULOS, V ;
GHORBANIAN, S ;
TYMAN, JHP ;
BROWN, RG ;
BRITTAIN, PI .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1990, (05) :837-842
[2]   Synthesis, spectroscopic and biological studies of a fluorescent Pt(II) (terpy) based 1,8-naphthalimide conjugate as a DNA targeting agent [J].
Banerjee, Swagata ;
Kitchen, Jonathan A. ;
Bright, Sandra A. ;
O'Brien, John E. ;
Williams, D. Clive ;
Kelly, John M. ;
Gunnlaugsson, Thorfinnur .
CHEMICAL COMMUNICATIONS, 2013, 49 (76) :8522-8524
[3]   The effect of the 4-amino functionality on the photophysical and DNA binding properties of alkyl-pyridinium derived 1,8-naphthalimides [J].
Banerjee, Swagata ;
Kitchen, Jonathan A. ;
Gunnlaugsson, Thorfinnur ;
Kelly, John M. .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2013, 11 (34) :5642-5655
[4]   Recent advances in the development of 1,8-naphthalimide based DNA targeting binders, anticancer and fluorescent cellular imaging agents [J].
Banerjee, Swagata ;
Veale, Emma B. ;
Phelan, Caroline M. ;
Murphy, Samantha A. ;
Tocci, Gillian M. ;
Gillespie, Lisa J. ;
Frimannsson, Daniel O. ;
Kelly, John M. ;
Gunnlaugsson, Thorfinnur .
CHEMICAL SOCIETY REVIEWS, 2013, 42 (04) :1601-1618
[5]   Microwave-assisted solvent-free synthesis of fluorescent naphthalimide dyes [J].
Bardajee, Ghasem R. .
DYES AND PIGMENTS, 2013, 99 (01) :52-58
[6]   Modular Construction of Fluorescent Lipophosphoramidates by Click Chemistry [J].
Berchel, Mathieu ;
Haelters, Jean-Pierre ;
Couthon-Gourves, Helene ;
Deschamps, Laure ;
Midoux, Patrick ;
Lehn, Pierre ;
Jaffres, Paul-Alain .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2011, 2011 (31) :6294-6303
[7]   Iridium complex triggered white-light-emitting gel and its response to cysteine [J].
Cao, Xinhua ;
Wu, Yongquan ;
Liu, Keyin ;
Yu, Xudong ;
Wu, Bo ;
Wu, Huazhou ;
Gong, Zuguang ;
Yi, Tao .
JOURNAL OF MATERIALS CHEMISTRY, 2012, 22 (06) :2650-2657
[8]   Synthesis and electronic spectra of new low-molecular weight compounds with possible application in electroluminescent layers [J].
Dobrikov, Georgi H. ;
Dobrikov, Georgi M. ;
Aleksandrova, Mariya .
CENTRAL EUROPEAN JOURNAL OF CHEMISTRY, 2011, 9 (06) :1126-1132
[9]   Why, on interaction of urea-based receptors with fluoride, beautiful colors develop [J].
Esteban-Gómez, D ;
Fabbrizzi, L ;
Licchelli, M .
JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (14) :5717-5720
[10]   A Multiligand Based Pd Catalyst for C-N Cross-Coupling Reactions [J].
Fors, Brett P. ;
Buchwald, Stephen L. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (45) :15914-15917