A Simple Method for the Synthesis of 3-Arylthieno[2,3-b]pyridines via Iodine-Mediated Cyclization of 3-(1-Arylalkenyl)-2-[(1-phenylethyl)sulfanyl]pyridines

被引:7
作者
Kobayashi, Kazuhiro [1 ]
Nakamura, Daizo [1 ]
Shiroyama, Yasuhiko [1 ]
Fukamachi, Shuhei [1 ]
Konishi, Hisatoshi [1 ]
机构
[1] Tottori Univ, Grad Sch Engn, Dept Chem & Biotechnol, Div Appl Chem, Tottori 6808552, Japan
来源
SYNTHESIS-STUTTGART | 2009年 / 13期
关键词
thieno[2,3-b]pyridines; iodine; 2-bromopyridines; cyclization; heterocycles; PYRIDINE; THIENOPYRIDINE; DERIVATIVES; AGENTS;
D O I
10.1055/s-0029-1216857
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
3-Arylthieno[2,3-b]pyridines are synthesized in a short four-step sequence from readily available 2-bromopyridines. The final and key step of the reported method involves an iodine-mediated 5-endo cyclization of 3-(1-arylalkenyl)-2-[(1-phenylethyl)sulfanyl]pyridines.
引用
收藏
页码:2179 / 2183
页数:5
相关论文
共 19 条
[11]  
MARSAIS F, 1982, J CHEM RES-S, P278
[12]   Bicyclic and tricyclic thiophenes as protein tyrosine phosphatase 1B inhibitors [J].
Moretto, AF ;
Kirincich, SJ ;
Xu, WX ;
Smith, MJ ;
Wan, ZK ;
Wilson, DP ;
Follows, BC ;
Binnun, E ;
Joseph-McCarthy, D ;
Foreman, K ;
Erbe, DV ;
Zhang, YL ;
Tam, SK ;
Tam, SY ;
Lee, J .
BIOORGANIC & MEDICINAL CHEMISTRY, 2006, 14 (07) :2162-2177
[13]   Evolution of the thienopyridine class of inhibitors of IκB kinase-β:: Part I:: Hit-to-lead strategies [J].
Morwick, Tina ;
Berry, Angela ;
Brickwood, Janice ;
Cardozo, Mario ;
Catron, Katrina ;
DeTuri, Molly ;
Emeigh, Jonathan ;
Homon, Carol ;
Hrapchak, Matt ;
Jacober, Stephen ;
Jakes, Scott ;
Kaplita, Paul ;
Kelly, Terence A. ;
Ksiazek, John ;
Liuzzi, Michel ;
Magolda, Ronald ;
Mao, Can ;
Marshall, Daniel ;
McNeil, Daniel ;
Prokopowicz, Anthony, III ;
Sarko, Christopher ;
Scouten, Erika ;
Sledziona, Cynthia ;
Sun, Sanxing ;
Watrous, Jane ;
Wu, Jiang Ping ;
Cywin, Charles L. .
JOURNAL OF MEDICINAL CHEMISTRY, 2006, 49 (10) :2898-2908
[14]   Synthesis of the fused heterobicycles 5-pyridin-2-yl-thieno[3,2-b]pyridine, 6-pyridin-2-yl-thieno[2,3-b]pyridine and 6-pyridin-2-yl-thieno[3,2-c]pyridine [J].
Nurkkala, LJ ;
Steen, RO ;
Dunne, SJ .
SYNTHESIS-STUTTGART, 2006, (08) :1295-1300
[15]  
Parnes JS, 2004, HETEROCYCLES, V63, P2199
[16]   An efficient one-pot synthesis of substituted 2-arylbenzo[b]thiophene derivatives [J].
Patel, MV ;
Rohde, JJ ;
Gracias, V ;
Kolasa, T .
TETRAHEDRON LETTERS, 2003, 44 (35) :6665-6667
[17]   Design, synthesis, SAR, and biological evaluation of new 4-(phenylamino)thieno[2,3-b]pyridine derivatives [J].
Rolim Bernardino, Alice Maria ;
Carlos da Silva Pinheiro, Luiz ;
Rangel Rodrigues, Carlos ;
Izabel Loureiro, Natalia ;
Carla Castro, Helena ;
Lanfredi-Rangel, Adriana ;
Sabatini-Lopes, Juliano ;
Cesar Borges, Julio ;
Maria Carvalho, Jane ;
Alves Romeiro, Gilberto ;
Francisco Ferreira, Vitor ;
Frugulhetti, Izabel C. P. P. ;
Vannier-Santos, Marcos Andre .
BIOORGANIC & MEDICINAL CHEMISTRY, 2006, 14 (16) :5765-5770
[18]   Free radical-mediated aryl amination:: A practical synthesis of (R)- and (S)-7-azaindoline α-amino acid [J].
Srinivasan, JM ;
Burks, HE ;
Smith, CR ;
Viswanathan, R ;
Johnston, JN .
SYNTHESIS-STUTTGART, 2005, (02) :330-333
[19]   Practical routes to 2,6-disubstituted pyridine derivatives [J].
Vandromme, Lucie ;
Reissig, Hans-Ulrich ;
Groeper, Susie ;
Rabe, Juergen P. .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2008, 2008 (12) :2049-2055