Synthesis of 3-Arylthieno[2,3-b]-, -[2,3-c]- or -[3,2-c]pyridines Utilizing an Interrupted Pummerer Reaction

被引：12
作者：
Kobayashi, Kazuhiro [1 ]
Suzuki, Teruhiko [1 ]
Horiuchi, Mai [1 ]
Shiroyama, Yasuhiko [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 | 2011年 / 18期
关键词：
thieno[2,3-b]pyridines; thieno[2,3-c]pyridines; thieno[3,2-c]pyridines; interrupted Pummerer reaction; acetic anhydride; MICROWAVE-ASSISTED SYNTHESIS; DERIVATIVES; THIENOPYRIDINES; INHIBITION; DISCOVERY;
D O I：
10.1055/s-0030-1260152
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
An efficient procedure for the synthesis of three types of thienopyridines has been developed. Thus, 3-(1-arylethenyl)-2-(ethylsulfinyl)pyridines, 4-(1-arylethenyl)-3-(ethylsulfinyl)pyridines, and 3-(1-arylethenyl)-4-(ethylsulfinyl)pyridines, which can be easily prepared from the respective aryl chloropyridinyl ketones in a three-step sequence, undergo an interrupted Pummerer reaction on treatment with excess acetic anhydride at temperatures ranging from 100 to 130 degrees C to give 3-arylthieno[2,3-b] pyridines, 3-aryl-thieno[2,3-c]pyridines, and 3-arylthieno[3,2-c]pyridines, respectively.
引用
收藏
页码：2897 / 2906
页数：10
相关论文
共 27 条
  • [1] Discovery of thienopyridines as Src-family selective Lck inhibitors
    Abbott, Lily
    Betschmann, Patrick
    Burchat, Andrew
    Calderwood, David J.
    Davis, Heather
    Hrnciar, Peter
    Hirst, Gavin C.
    Li, Biqin
    Morytko, Michael
    Mullen, Kelly
    Yang, Bryant
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2007, 17 (05) : 1167 - 1171
  • [2] MICROWAVE-ASSISTED SYNTHESIS OF 3-METHYLISOTHIAZOLO[5,4-b]PYRIDINE AND VARIOUS 2-AMINO DERIVATIVES OF THIENO[2,3-b]PYRIDINE AND 1-(2-AMINOPYRIDIN-3-YL)ETHANONE
    Ankati, Haribabu
    Biehl, Edward R.
    [J]. HETEROCYCLES, 2010, 80 (02) : 1291 - 1302
  • [3] Identification of a selective thieno[2,3-c]pyridine inhibitor of COT kinase and TNF-α production
    Cusack, Kevin
    Allen, Hamish
    Bischoff, Agnieszka
    Clabbers, Anca
    Dixon, Richard
    Fix-Stenzel, Shannon
    Friedman, Michael
    Gaumont, Yvette
    George, Dawn
    Gordon, Thomas
    Grongsaard, Pintipa
    Janssen, Bernd
    Jia, Yong
    Moskey, Maria
    Quinn, Christopher
    Salmeron, Andres
    Thomas, Christine
    Wallace, Grier
    Wishart, Neil
    Yu, Zhengtian
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2009, 19 (06) : 1722 - 1725
  • [4] Eineairy M. A. A., 2010, PHOSPHORUS SULFUR, V185, P469
  • [5] Synthesis and antibacterial activity of some new ethyl thionicotinates, thieno[2,3-b]pyridines, pyrido[3′,2′:4,5]thieno[3,2-d]pyrimidines, and pyrido[3′,2′:4,5]thieno[3,2-d][1,2,3]triazines containing sulfonamide moieties
    Gad-Elkareem, Mohamed A. M.
    El-Adasy, Abu-Bakr A. A. M.
    [J]. PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2010, 185 (02) : 411 - 421
  • [6] Discovery of thieno[2,3-c]pyridines as potent COT inhibitors
    George, Dawn
    Friedman, Michael
    Allen, Hamish
    Argiriadi, Maria
    Barberis, Claude
    Bischoff, Agnieszka
    Clabbers, Anca
    Cusack, Kevin
    Dixon, Richard
    Fix-Stenzel, Shannon
    Gordon, Thomas
    Janssen, Bernd
    Jia, Yong
    Moskey, Maria
    Quinn, Christopher
    Salmeron, Jose-Andres
    Wishart, Neil
    Woller, Kevin
    Yu, Zhengtian
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2008, 18 (18) : 4952 - 4955
  • [7] REGIOSELECTIVE ORTHO LITHIATION OF HALOPYRIDINES
    GRIBBLE, GW
    SAULNIER, MG
    [J]. TETRAHEDRON LETTERS, 1980, 21 (43) : 4137 - 4140
  • [8] Thienopyridine urea inhibitors of KDR kinase
    Heyman, H. Robin
    Frey, Robin R.
    Bousquet, Peter F.
    Cunha, George A.
    Moskey, Maria D.
    Ahmed, Asma A.
    Soni, Niru B.
    Marcotte, Patrick A.
    Pease, Lori J.
    Glaser, Keith B.
    Yates, Melinda
    Bouska, Jennifer J.
    Albert, Daniel H.
    Black-Schaefer, Candace L.
    Dandliker, Peter J.
    Stewart, Kent D.
    Rafferty, Paul
    Davidsen, Steven K.
    Michaelides, Michael R.
    Curtin, Michael L.
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2007, 17 (05) : 1246 - 1249
  • [9] ONE-POT SYNTHESIS OF THREE TYPES OF 2,3-DISUNSTITUTED THIENOPYRIDINES FROM HALOPYRIDINYL KETONES
    Kobayashi, Kazuhiro
    Kozuki, Taketoshi
    Konishi, Hisatoshi
    [J]. HETEROCYCLES, 2009, 78 (12) : 2993 - 3000
  • [10] 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
    Kobayashi, Kazuhiro
    Nakamura, Daizo
    Shiroyama, Yasuhiko
    Fukamachi, Shuhei
    Konishi, Hisatoshi
    [J]. SYNTHESIS-STUTTGART, 2009, (13): : 2179 - 2183
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