Regioselective synthesis of salicylates and acetophenones by formal [3+3]-cyclocondensations of 3-oxoorthoesters with 1,3-bis(trimethylsilyloxy)-1,3-butadienes

被引:0
|
作者
Guetlein, Joerg-Peter [1 ]
Lubbe, Mathias [1 ]
Feist, Holger [1 ]
Villinger, Alexander [1 ]
Langer, Peter [1 ,2 ]
机构
[1] Univ Rostock, Inst Chem, Albert Einstein Str 3a, D-18059 Rostock, Germany
[2] Leibniz Inst Katalyse eV, Albert Einstein Str 29a, D-18059 Rostock, Germany
关键词
cyclizations; phenols; regioselectivity; salicylates; silyl enol ethers; ENOL SILYL ETHERS; IN-VITRO; ANTIOXIDANT ACTIVITIES; PLANT POLYPHENOLS; MEDICINAL-PLANTS; PHENOLIC-ACIDS; FLAVONOIDS; CYCLIZATION; EXTRACTION; CHEMISTRY;
D O I
10.1515/znb-2020-0114
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
A variety of 4-methoxysalicylates and related polyketide-type phenols are regioselectively prepared by formal [3+3] cyclocondensations of 1,3-bis(trimethylsilyloxy)-1,3-butadienes with 3-oxo-orthoesters. Cycloalkyl-substituted salicylates were prepared for the first time.
引用
收藏
页码:1 / 26
页数:26
相关论文
共 50 条
  • [1] Regioselective Synthesis of Polyketide-Type Phenols by Formal [3+3]-Cyclocondensations of 1,3-Bis(silyloxy)-1,3-butadienes with 3-Oxoorthoesters
    Lubbe, Mathias
    Guetlein, Joerg-Peter
    Reinke, Helmut
    Langer, Peter
    [J]. SYNLETT, 2008, (17) : 2671 - 2673
  • [2] Regioselective Synthesis of 5-(2-Methoxyethyl)biphenyls by Formal [3+3] Cyclocondensations of 1,3-Bis(trimethylsilyloxy)-1,3-butadienes
    Bendrath, Franziska
    Specowius, Verena
    Abilov, Zharylkasyn A.
    Saghyan, Ashot. S.
    Fischer, Christine
    Langer, Peter
    [J]. ZEITSCHRIFT FUR NATURFORSCHUNG SECTION B-A JOURNAL OF CHEMICAL SCIENCES, 2013, 68 (04): : 378 - 382
  • [3] Regioselective synthesis of rare 3-halomethylphenols based on formal [3+3] cyclizations of 1,3-bis(trimethylsilyloxy)-1,3-butadienes
    Lubbe, Mathias
    Mamat, Constantin
    Langer, Peter
    [J]. SYNLETT, 2008, (11) : 1684 - 1686
  • [4] Regioselective synthesis of 3-(methylthio)phenols by formal [3+3]-cyclocondensations of 3-oxo-bis(methylthio)ketenacetals with 1,3-bis(trimethylsilyloxy)-1,3-butadienes and 1,3-dicarbonyl dianions
    Lubbe, Mathias
    Bendrath, Franziska
    Trabhardt, Tiana
    Villinger, Alexander
    Fischer, Christine
    Langer, Peter
    [J]. TETRAHEDRON, 2013, 69 (29) : 5998 - 6007
  • [5] Regioselective synthesis of amino- and nitroarenes based on [3+3] cyclocondensations of 1,3-bis(silyloxy)-1,3-butadienes
    Riahi, Abdolmajid
    Shkoor, Mohanad
    Fatunsin, Olumide
    Yawer, Mirza A.
    Hussain, Ibrar
    Fischer, Christine
    Langer, Peter
    [J]. TETRAHEDRON, 2009, 65 (45) : 9300 - 9315
  • [6] First Synthesis of 5-Cyanosalicylates by Formal [3+3] Cyclocondensations of 1,3-Bis(silyloxy)-1,3-butadienes
    Riahi, Abdolmajid
    Fatunsin, Olumide
    Shkoor, Mohanad
    Dede, Ruediger
    Reinke, Helmut
    Fischer, Christine
    Langer, Peter
    [J]. SYNTHESIS-STUTTGART, 2009, (10): : 1623 - 1634
  • [7] Regioselective synthesis of functionalized 3-(methylthio)phenols by the first formal [3+3] cyclocondensations of 1,3-bis(trimethylsilyloxy)-1,3-butadienes with 1,1-bis(methylthio)-1-en-3-ones
    Lubbe, Mathias
    Klassen, Renske
    Trabhardt, Tiana
    Villinger, Alexander
    Langer, Peter
    [J]. SYNLETT, 2008, (15) : 2331 - 2333
  • [8] Competing Regiodirecting Effects of Ester and Aryl Groups in [3+3] Cyclocondensations of 1,3-Bis(trimethylsilyloxy)-1,3-butadienes: Regioselective Synthesis of 3-Hydroxyphthalates and 2-Hydroxyterephthalates
    Shkoor, Mohanad
    Fatunsin, Olumide
    Riahi, Abdolmajid
    Lubbe, Mathias
    Reim, Stefanie
    Sher, Muhammad
    Villinger, Alexander
    Fischer, Christine
    Langer, Peter
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2010, 2010 (19) : 3732 - 3742
  • [9] 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
    [J]. ZEITSCHRIFT FUR NATURFORSCHUNG SECTION B-A JOURNAL OF CHEMICAL SCIENCES, 2013, 68 (09): : 1021 - 1030
  • [10] Synthesis of functionalized diaryl selenides by the first [3+3] cyclocondensations of 1,3-bis(silyloxy)-1,3-butadienes with organoselenium compounds
    Shkoor, Mohanad
    Fatunsin, Olumide
    Riahi, Abdolmajid
    Villinger, Alexander
    Langer, Peter
    [J]. TETRAHEDRON LETTERS, 2009, 50 (41) : 5726 - 5728