Synthesis of symmetrical amino and aminomethyl derivatives of Troger's base via Pd-catalyzed C-C and C-N bond formation

被引:31
作者
Didier, Delphine [1 ]
Sergeyev, Sergey [1 ]
机构
[1] Univ Libre Bruxelles, Lab Chim Polymeres, B-1050 Brussels, Belgium
关键词
Troger's base; cross coupling; amination; cyanation;
D O I
10.1016/j.tet.2007.02.032
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
In this paper, we report the synthesis of amino and aminomethyl derivatives of Troger's base (+/-)-1 and (+/-)-2. The key steps in the synthesis of (+/-)-1 and (+/-)-2 are Pd-catalyzed amination and cyanation, respectively, of the easily accessible dihalo derivatives (+/-)-3. These compounds are important intermediates in the synthesis of new ligands and building blocks for H-bonded supramolecular architectures. (C) 2007 Elsevier Ltd. All rights reserved.
引用
收藏
页码:3864 / 3869
页数:6
相关论文
共 31 条
[1]   CHEMISTRY OF SYNTHETIC RECEPTORS AND FUNCTIONAL-GROUP ARRAYS .10. ORDERLY FUNCTIONAL-GROUP DYADS - RECOGNITION OF BIOTIN AND ADENINE-DERIVATIVES BY A NEW SYNTHETIC HOST [J].
ADRIAN, JC ;
WILCOX, CS .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (20) :8055-8057
[2]   THE CHEMISTRY OF SYNTHETIC RECEPTORS AND FUNCTIONAL GROUP ARRAYS .19. GENERAL EFFECTS OF BINDING-SITE WATER EXCLUSION ON HYDROGEN-BOND BASED MOLECULAR RECOGNITION SYSTEMS - A CLOSED BINDING-SITE IS LESS AFFECTED BY ENVIRONMENTAL-CHANGES THAN AN OPEN SITE [J].
ADRIAN, JC ;
WILCOX, CS .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (04) :1398-1403
[3]  
[Anonymous], 2002, HDB ORGANOPALLADIUM
[4]   α-amino acid Troger base derivatives, possible conformationally restricted scaffolds? [J].
Bew, Sean P. ;
Legentil, Laurent ;
Scholier, Vincent ;
Sharma, Sunil V. .
CHEMICAL COMMUNICATIONS, 2007, (04) :389-391
[5]  
DOLENSKY B, IN PRESS ADV HETEROC
[6]   CYANATION OF AROMATIC HALIDES [J].
ELLIS, GP ;
ROMNEYALEXANDER, TM .
CHEMICAL REVIEWS, 1987, 87 (04) :779-794
[7]   Molecular recognition: Chain length selectivity studies of dicarboxylic acids by the cavity of a new Troger's base receptor [J].
Goswami, S ;
Ghosh, K .
TETRAHEDRON LETTERS, 1997, 38 (25) :4503-4506
[8]   Troger's base molecular scaffolds in dicarboxylic acid recognition [J].
Goswami, S ;
Ghosh, K ;
Dasgupta, S .
JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (07) :1907-1914
[9]   Synthesis of dihalo-substituted analogues of Troger's base from ortho- and meta-substituted anilines [J].
Hansson, A ;
Jensen, J ;
Wendt, OF ;
Wärnmark, K .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2003, 2003 (16) :3179-3188
[10]   Room-temperature palladium-catalyzed amination of aryl bromides and chlorides and extended scope of aromatic C-N bond formation with a commercial ligand [J].
Hartwig, JF ;
Kawatsura, M ;
Hauck, SI ;
Shaughnessy, KH ;
Alcazar-Roman, LM .
JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (15) :5575-5580