Facile synthesis of 1,8-naphthalimides in palladium-catalysed aminocarbonylation of 1,8-diiodo-naphthalene

被引：31

作者：

Takacs, Attila ^{[1
]}

Acs, Peter ^{[1
]}

Kollar, Laszlo ^{[1
]}

机构：

[1] Univ Pecs, Dept Inorgan Chem, H-7624 Pecs, Hungary

来源：

TETRAHEDRON | 2008年 / 64卷 / 06期

基金：

匈牙利科学研究基金会;

关键词：

D O I：

10.1016/j.tet.2007.10.026

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

1,8-Diiodo-naphthalene was aminocarbonylated with various primary and secondary amines in the presence of palladium(0) complexes formed in situ from palladium(II) acetate and triphenylphosphine. In the case of primary amines, depending on the amine to substrate ratio, two types of products have been obtained in highly chemoselective reaction: dicarboxamides and N-substituted imides have been formed at high and low amine to substrate ratio, respectively. The reaction tolerates the ester functionality, so that amino acid esters could serve as N-nucleophiles and in this way, naphthalimides possessing stereogenic centre in the N-substituent could be synthesised. (c) 2007 Elsevier Ltd. All rights reserved.

引用

页码：983 / 987

页数：5

共 50 条

[11] Palladium-catalysed amination of 1,8-and 1,5-dichloroanthracenes and 1,8-and 1,5-dichloroanthraquinones [J].

Beletskaya, IP ;

Bessmertnykh, AG ;

Averin, AD ;

Denat, F ;

Guilard, R .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2005, 2005 (02) :281-305

[12] Design and Synthesis of Some 1,8-Naphthalimides as Fluorescence Probes for Transition Metal Ions [J].

Wang, Yingchun ;

Zhang, Ye ;

Yi, Xianghui ;

Qin, Wen .

ASIAN JOURNAL OF CHEMISTRY, 2012, 24 (01) :323-326

[13] A Gram Scale Synthesis of 3,4-Dihalogen Substituted 1,8-Naphthalimides [J].

Anastasova, Denitsa ;

Mutovska, Monika ;

Simeonova, Natali ;

Zagranyarska, Irena ;

Vlahova, Zlatina ;

Stoyanov, Stanimir ;

Zagranyarski, Yulian .

MOLBANK, 2024, 2024 (04)

[14] Synthesis of highly photostable blue-emitting 1,8-naphthalimides and their acrylonitrile copolymers [J].

Bojinov, Vladimir B. ;

Simeonov, Danail B. .

POLYMER DEGRADATION AND STABILITY, 2010, 95 (01) :43-52

[15] The plausible aromaticity of 1,8-naphthalimides:: The enthalpy of formation of N-methyl-1,8-naphthalimide [J].

Roux, MV ;

Jiménez, P ;

Dávalos, JZ ;

Martín-Luengo, MA ;

Rotello, VM ;

Cuello, AO ;

Liebman, JF .

STRUCTURAL CHEMISTRY, 2000, 11 (01) :1-7

[16] Synthesis and spectral-luminescent characteristics of N-substituted 1,8-naphthalimides [J].

Prezhdo, Oleg V. ;

Uspenskii, Boris V. ;

Prezhdo, Victor V. ;

Boszczyk, Wojciech ;

Distanov, Vitalii B. .

DYES AND PIGMENTS, 2007, 72 (01) :42-46

[17] Protein crosslinking by 1,8-naphthalimides: influence of the 4-substituent [J].

Woods, RJ ;

Zhang, JX ;

Green, CR ;

Kane, RR .

ARKIVOC, 2003, :109-118

[18] Photophysical properties of new polymerizable 1,8-naphthalimides and their copolymers with methylmethacrylate [J].

Grabchev, I ;

Staneva, D .

ZEITSCHRIFT FUR NATURFORSCHUNG SECTION A-A JOURNAL OF PHYSICAL SCIENCES, 2003, 58 (9-10) :558-562

[19] PHOTOPHYSICS OF SUBSTITUTED 1,8-NAPHTHALIMIDES BOUND TO A POLY(ALLYLAMINE) POLYMER [J].

CAO, T ;

WEBBER, SE .

MACROMOLECULES, 1991, 24 (01) :79-86

[20] The Plausible Aromaticity of 1,8-Naphthalimides: The Enthalpy of Formation of N-Methyl-1,8-Naphthalimide [J].

Maria Victoria Roux ;

Pilar Jiménez ;

Juan Z. Dávalos ;

Maria Angeles Martín-Luengo ;

Vincent M. Rotello ;

Alejandro O. Cuello ;

Joel F. Liebman .

Structural Chemistry, 2000, 11 :1-7

← 1 2 3 4 5 →