One-pot synthesis of 6-(pyridyl)salicylates by formal [3+3] cyclizations of 1,3-bis(silyl enol ethers) with 3-pyridyl-3-silyloxy-2-en-1-ones

被引：2
|
作者：
Yawer, Mirza A. [1 ]
Riahi, Abdolmajid [1 ,2 ]
Adeel, Muhammad [1 ]
Hussain, Ibrar [1 ]
Fischer, Christine [2 ]
Langer, Peter [1 ,2 ]
机构：
[1] Univ Rostock, Inst Chem, D-18059 Rostock, Germany
[2] Univ Rostock, Leibniz Inst Katalyse EV, D-18059 Rostock, Germany
来源：
SYNTHESIS-STUTTGART | 2008年 / 08期
关键词：
cyclizations; heterocycles; regioselectivity; pyridines; silyl enol ethers;
D O I：
10.1055/s-2008-1042949
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
6-(Pyridyl)salicylates were regioselectively prepared by formal [3+3] cyclization of 1,3-bis(silyl enol ethers) with 3-(pyridyl)-3-silyloxy-2-en-1-ones. These reactions represent what are, to the best of our knowledge, the first [3+3] cyclizations of 1,3-bis(silyl enol ethers) with heterocyclic substrates.
引用
收藏
页码：1276 / 1282
页数：7
相关论文
共 50 条
  • [1] Synthesis of diaryl ethers based on one-pot [3+3] cyclizations of 1,3-bis(silyl enol ethers)
    Sher, Muhammad
    Ahmed, Zafar
    Rashid, Muhammad A.
    Fischer, Christine
    Spannenberg, Anke
    Langer, Peter
    TETRAHEDRON, 2007, 63 (23) : 4929 - 4936
  • [2] One-pot synthesis of aryl fluorides by [3+3] cyclization of 1,3-bis(silyl enol ethers) with 2-fluoro-3-silyloxy-2-en-1-ones
    Pundt, Thomas
    Lau, Matthias
    Hussain, Ibrar
    Yawer, Mirza A.
    Reinke, Helmut
    Langer, Peter
    TETRAHEDRON LETTERS, 2007, 48 (15) : 2745 - 2747
  • [3] One-pot synthesis of functionalized carbacycles by formal [3+3] cyclizations of 1,3-bis(silyl enol ethers) with 1,3-dielectrophiles
    Feist, Holger
    Langer, Peter
    SYNTHESIS-STUTTGART, 2007, (03): : 327 - 347
  • [4] Synthesis of phthalates and isophthalates by [3+3] cyclizations of 1,3-bis(silyl enol ethers) with 3-(silyloxy)alk-2-en-1-ones
    Reim, Stefanie
    Lubbe, Mathias
    Langer, Peter
    TETRAHEDRON LETTERS, 2006, 47 (38) : 6751 - 6752
  • [5] Synthesis of Bicyclic Salicylates by [3+3] Cyclization of 1,3-Bis(Silyl Enol Ethers) with Cyclic 3-(Silyloxy)alk-2-en-1-ones
    Hoettecke, Nicole
    Reinke, Helmut
    Fischer, Christine
    Langer, Peter
    ZEITSCHRIFT FUR NATURFORSCHUNG SECTION B-A JOURNAL OF CHEMICAL SCIENCES, 2009, 64 (06): : 699 - 706
  • [6] Synthesis of dibenzo[b,d]pyran-6-ones based on [3+3] cyclizations of 1,3-bis(silyl enol ethers) with 3-silyloxy-2-en-1-ones
    Hussain, Ibrar
    Nguyen, Van Thi Hong
    Yawer, Mirza Arfan
    Dang, Tuan Thanh
    Fischer, Christine
    Reinke, Helmut
    Langer, Peter
    JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (16): : 6255 - 6258
  • [7] Synthesis of 6-(perfluoroalkyl)salicylates by [3+3] cyclization of 1,3-bis(silyl enol ethers) with 3-ethoxy-1-(perfluoroalkyl)prop-2-en-1-ones
    Lubbe, Mathias
    Mamat, Constantin
    Fischer, Christine
    Langer, Peter
    TETRAHEDRON, 2007, 63 (02) : 413 - 418
  • [8] Efficient synthesis of salicylates by catalytic [3+3] cyclizations of 1,3-bis(silyl enol ethers) with 1,1,3,3-tetramethoxypropane
    Sher, Muhammad
    Dang, T. H. Tam
    Ahmed, Zafar
    Rashid, Muhammad A.
    Fischer, Christine
    Langer, Peter
    JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (16): : 6284 - 6286
  • [9] Synthesis of functionalized diaryl ethers by [3+3] cyclization of 1,3-bis(silyl enol ethers) with 2-aryloxy-3-(silyloxy)alk-2-en-1-ones
    Ahmed, Zafar
    Langer, Peter
    SYNLETT, 2006, (19) : 3361 - 3363
  • [10] Synthesis of Functionalized Diaryldiazenes by Formal [3+3] Cyclizations of 1,3-Bis(silyloxy)-1,3-butadienes with 2-Aryldiazenyl-3-silyloxy-2-en-1-ones
    Hefner, Jennifer
    Ladzik, Simone
    Hein, Martin
    Harms, Manuela
    Lalk, Michael
    Kelzhanova, Nazken
    Saginayev, Amanzhan T.
    Rahman, Qamar
    Villinger, Alexander
    Fischer, Christine
    Langer, Peter
    ZEITSCHRIFT FUR NATURFORSCHUNG SECTION B-A JOURNAL OF CHEMICAL SCIENCES, 2014, 69 (08): : 924 - 944
12345