A facile S-transalkylation of 2,2′-bipyridine alkyl sulfides -: a new tool for the synthesis of annulated biheterocycles

被引:18
作者
Branowska, D [1 ]
Rykowski, A [1 ]
Wysocki, W [1 ]
机构
[1] Univ Podlasie, Dept Chem, PL-08110 Siedlce, Poland
关键词
S-transalkylation; annulated dicluaternary 2,2 '-bipyridinium salts;
D O I
10.1016/j.tetlet.2005.07.062
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A simple and efficient synthesis of annulated 2,2'-bipyridinium salts with attached dihydrothiazole or dihydro-1,3-thiazine rings has been developed through tandem S-transalkylation/intramolecular ring closure of 2,2'-bipyridine alkyl sulfides. The structures were confirmed by X-ray crystallographic analysis. (c) 2005 Elsevier Ltd. All rights reserved.
引用
收藏
页码:6223 / 6226
页数:4
相关论文
共 21 条
[1]  
Balasubramanian M., 1996, COMPREHENSIVE HETERO, V5, P245, DOI 10.1016/B978-008096518-5.00109
[2]   Synthesis of unsymmetrical annulated 2,2′-bipyridine analogues with attached cycloalkene and piperidine rings via sequential Diels-Alder reaction of 5,5′-bi-1,2,4-triazines [J].
Branowska, D .
MOLECULES, 2005, 10 (01) :265-273
[3]   Application of intramolecular cycloaddition/retro cycloaddition reactions for the synthesis of unsymmetrical 2,2′-bipyridine and 2-benzofuropyrazin-2-ylpyridine analogues [J].
Branowska, D .
TETRAHEDRON, 2004, 60 (28) :6021-6027
[4]   A facile route to symmetrical and unsymmetrical cycloalkeno[c]fused 2,2′-bipyridine ligands via inverse electron demand Diels-Alder reaction of 5,5′-bi-1,2,4-triazines [J].
Branowska, D .
SYNTHESIS-STUTTGART, 2003, (13) :2096-2100
[5]  
Branowska D, 2003, POL J CHEM, V77, P1149
[6]  
Branowska D, 2002, SYNLETT, P1892
[7]  
BRANOWSKA D, 2005, MOLECULES, V10, P247
[8]   Lanthanide tags for time-resolved luminescence microscopy displaying improved stability and optical properties [J].
Charbonnière, L ;
Ziessel, R ;
Guardigli, M ;
Roda, A ;
Sabbatini, N ;
Cesario, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (10) :2436-2437
[9]   Synthesis of mono-, bis- and tris-tridentate ligands based on 5′-substituted-2,2′-bipyridine-6-carboxylic acid [J].
Charbonnière, LJ ;
Weibel, N ;
Ziessel, RF .
TETRAHEDRON LETTERS, 2001, 42 (04) :659-662
[10]   PHOTOINDUCED HYDROGEN EVOLUTION BY A ZWITTERIONIC DIQUAT ELECTRON-ACCEPTOR - THE FUNCTIONS OF SIO2 COLLOID IN CONTROLLING THE ELECTRON-TRANSFER PROCESS [J].
DEGANI, Y ;
WILLNER, I .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1983, 105 (20) :6228-6233