Regioselective synthesis of 5-alkylsalicylates, 5-alkyl-2-hydroxy-acetophenones, and 5-alkyl-2-hydroxy-benzophenones by [3+3] cyclization of 1,3-bis(silyl enol ethers) with 2-alkyl-1,1,3,3-tetraethoxypropanes

被引:17
|
作者
Mamat, Constantin
Buettner, Stefan
Trabhardt, Tiana
Fischer, Christine
Langer, Peter
机构
[1] Univ Rostock, Inst Chem, D-18059 Rostock, Germany
[2] Univ Rostock, Leibniz Inst Katalyse, D-18059 Rostock, Germany
来源
JOURNAL OF ORGANIC CHEMISTRY | 2007年 / 72卷 / 16期
关键词
D O I
10.1021/jo070847e
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A variety of 5-alkylsalicylates, 5-alkyl-2-hydroxy-acetophenones, and 5-alkyl-2-hydroxy-benzophenones was regioselectively prepared by TiCl4 mediated formal [3 + 3] cyclization of 1,3-bis(silyl enol ethers) with 2-alkyl-1,1,3,3-tetraethoxypropanes.
引用
收藏
页码:6273 / 6275
页数:3
相关论文
共 50 条
  • [1] SYNTHESES AND REACTIONS OF 2-ALKYL-1,3-CYCLOPENTANEDIONES (2-ALKYL-3-HYDROXY-2-CYCLOPENTEN-1-ONES)
    SCHICK, H
    EICHHORN, I
    SYNTHESIS-STUTTGART, 1989, (07): : 477 - 492
  • [2] SYNTHESIS AND ABSOLUTE STEREOCHEMISTRY OF 5-ALKYL-5-(3'-HYDROXY-1'-METHYLBUTYL)BARBITURIC ACID AND 5-ALKYL-5-(3'-HYDROXY-1'-METHYLBUTYL)-2-THIOBARBITURIC ACIDS
    CARROLL, FI
    MITCHELL, GN
    JOURNAL OF MEDICINAL CHEMISTRY, 1975, 18 (01) : 37 - 41
  • [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] 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
  • [5] SYNTHESIS OF 1-ALKYL-3-HYDROXY-2-PHENYLAZETIDINES
    TODA, T
    KARIKOMI, M
    OHSHIMA, M
    YOSHIDA, M
    HETEROCYCLES, 1992, 33 (02) : 511 - 514
  • [6] Synthesis of (S, S)-1, 5-bis(4-alkyl-5-hydroxy-2-oxo-3-azapentyl)-1, 5-diazacyclooetane
    Shang, ZL
    Shang, ZC
    Yu, QS
    CHINESE CHEMICAL LETTERS, 2001, 12 (09) : 769 - 770
  • [7] Synthesis of functionalized acetophenones by [3+3] cyclizations of 1,3-bis-silyl enol ethers with 2-acetyl-3-silyloxyalk-2-en-1-ones
    Dede, R
    Langer, P
    TETRAHEDRON LETTERS, 2004, 45 (50) : 9177 - 9179
  • [8] 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
  • [9] 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
  • [10] Synthesis of 2-Hydroxy-5-methoxy-3-alkyl-1,4-benzoquinones
    Wu, Liqiang
    Yang, Chunguang
    Yang, Limin
    ASIAN JOURNAL OF CHEMISTRY, 2009, 21 (09) : 7005 - 7011