Pyridinium N-heteroarylaminides: synthesis of N-heteroarylpolyamines

被引:6
作者
Castillo, Rafael R. [1 ]
Cordoba, Marta [1 ]
Luisa Izquierdo, M. [1 ]
Alvarez-Builla, Julio [1 ]
机构
[1] Univ Alcala de Henares, Dept Quim Organ, Madrid 28871, Spain
关键词
REGIOSELECTIVE SYNTHESIS; MOLECULAR RECOGNITION; POLYAMINES; EFFICIENT; AGENTS; MILD;
D O I
10.1016/j.tet.2009.09.079
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The synthesis of a set of new N-heteroarylpolyamines is reported. A multiple and regioselective alkylation on the exo nitrogen of pyridinium N-(heteroaryl)aminides with several polybromo compounds, followed by a clean N-N bond reduction of the corresponding pyridinium salts, provides an easy and general method to obtain the title compounds. (C) 2009 Elsevier Ltd. All rights reserved.
引用
收藏
页码:9782 / 9790
页数:9
相关论文
共 36 条
[11]   Pyridinium N-heteroarylaminides:: synthesis of N-heteroaryltetramines based on 1,6-bis(phenoxy)hexane and 1,3-bis(phenoxymethyl)benzene [J].
Castillo, Rafael ;
Izquierdo, M. Luisa ;
Alvarez-Builla, Julio .
TETRAHEDRON LETTERS, 2007, 48 (33) :5899-5903
[12]   Synthesis and evaluation of novel polyaminocarboxylate-based antitumor agents [J].
Chon, Hyun-Soon ;
Ma, Xiang ;
Lee, Haisung ;
Bui, Phuong ;
Song, Hyun A. ;
Birch, Noah .
JOURNAL OF MEDICINAL CHEMISTRY, 2008, 51 (07) :2208-2215
[13]   Synthesis and evaluation of novel macrocyclic and acyclic ligands as contrast enhancement agents for magnetic resonance imaging [J].
Chong, HS ;
Garmestani, K ;
Bryant, LH ;
Milenic, DE ;
Overstreet, T ;
Birch, N ;
Le, T ;
Brady, ED ;
Brechbiel, MW .
JOURNAL OF MEDICINAL CHEMISTRY, 2006, 49 (06) :2055-2062
[14]   Deuterated ammonium formate as deuterium source in a mild catalytic deuterium transfer reaction of pyridines, pyrazines and isoquinolines [J].
Derdau, V .
TETRAHEDRON LETTERS, 2004, 45 (48) :8889-8893
[15]  
Gilat SL, 1999, ANGEW CHEM INT EDIT, V38, P1422, DOI 10.1002/(SICI)1521-3773(19990517)38:10<1422::AID-ANIE1422>3.0.CO
[16]  
2-V
[17]   Methylazacalixpyridines: Remarkable bridging nitrogen-tuned conformations and cavities with unique recognition properties [J].
Gong, Han-Yuan ;
Zhang, Xiao-Hang ;
Wang, De-Xian ;
Ma, Hong-Wei ;
Zheng, Qi-Yu ;
Wang, Mei-Xiang .
CHEMISTRY-A EUROPEAN JOURNAL, 2006, 12 (36) :9262-9275
[18]   Polyamines as clinical laboratory tools [J].
Gugliucci, A .
CLINICA CHIMICA ACTA, 2004, 344 (1-2) :23-35
[19]   A general ruthenium-catalyzed synthesis of aromatic Amines [J].
Hollmann, Dirk ;
Baehn, Sebastian ;
Tillack, Annegret ;
Beller, Matthias .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (43) :8291-8294
[20]   Heck reactions: a caveat on the use of palladium(II) PCP-type catalysts [J].
Kiewel, K ;
Liu, YS ;
Bergbreiter, DE ;
Sulikowski, GA .
TETRAHEDRON LETTERS, 1999, 40 (51) :8945-8948