Synthesis of functionalized acetophenones by [3+3] cyclizations of 1,3-bis-silyl enol ethers with 2-acetyl-3-silyloxyalk-2-en-1-ones

被引：21
|
作者：
Dede, R [1 ]
Langer, P [1 ]
机构：
[1] Univ Greifswald, Inst Chem & Biochem Ernst Moritz Arndt, D-17487 Greifswald, Germany
来源：
TETRAHEDRON LETTERS | 2004年 / 45卷 / 50期
关键词：
acetophenones; cyclizations; regioselectivity; silyl enol ethers;
D O I：
10.1016/j.tetlet.2004.10.104
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The TiCl4 mediated cyclization of 1,3-bis-silyl enol ethers with 2-acetyl-1-silyloxybut-1-en-3-one and 3-acetyl-4-silyloxypcnt-3-en-2-one, readily prepared from 3-formyl(acetylacetone) and triacetyl methane, afforded a variety of functionalized acetophenones. (C) 2004 Published by Elsevier Ltd.
引用
收藏
页码：9177 / 9179
页数：3
相关论文
共 50 条
  • [1] Synthesis of functionalized p-dihydrobenzoquinones and p-benzoquinones based on [3+3] cyclizations of 1,3-bis-silyl enol ethers
    Ahmed, Z
    Fischer, C
    Spannenberg, A
    Langer, P
    TETRAHEDRON, 2006, 62 (20) : 4800 - 4806
  • [2] 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
  • [3] 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
  • [4] 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
  • [5] Synthesis of functionalized 4-chlorophenols and 1,4-dihydroquinones by [3+3] cyclization of 1,3-bis-silyl enol ethers with 2-chloro- and 2-acyloxy-3-(silyloxy)alk-2-en-1-ones
    Ahmed, Z
    Langer, P
    TETRAHEDRON LETTERS, 2006, 47 (04) : 417 - 419
  • [6] Regioselective synthesis of 2-acetyl- and 2-alkoxycarbonyl-3-(trifluoromethyl)phenols by [3+3] cyclization of 1,3-bis-silyl enol ethers with 4-ethoxy- and 4-silyloxy-1,1,1-trifluoroalk-3-en-2-ones
    Mamat, C
    Pundt, T
    Schmidt, A
    Langer, P
    TETRAHEDRON LETTERS, 2006, 47 (13) : 2183 - 2185
  • [7] 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
  • [8] 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
  • [9] 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
    Yawer, Mirza A.
    Riahi, Abdolmajid
    Adeel, Muhammad
    Hussain, Ibrar
    Fischer, Christine
    Langer, Peter
    SYNTHESIS-STUTTGART, 2008, (08): : 1276 - 1282
  • [10] Synthesis of Functionalized Acetophenones by Formal [3+3] Cyclocondensations of 1,3-Bis(silyloxy)-1,3-butadienes with 3-Alkoxy- and 3-Silyloxy-2-acetyl-2-en-1-ones
    Dede, Ruediger
    Riahi, Abdolmajid
    Shkoor, Mohanad
    Yawer, Mirza A.
    Hussain, Ibrar
    Kelzhanova, Nazken
    Abilov, Zharylkasyn A.
    Falodun, Abiodun
    Goerls, Helmar
    Langer, Peter
    ZEITSCHRIFT FUR NATURFORSCHUNG SECTION B-A JOURNAL OF CHEMICAL SCIENCES, 2013, 68 (09): : 1021 - 1030
12345