NOVEL SYNTHESIS OF THIOALKOXY-SUBSTITUTED OXA[9]HELICENES BY THE REACTION OF HELICAL QUINONES WITH THIOLS

被引:14
作者
Salim, Mohammad [1 ,2 ]
Kimura, Takao [1 ]
Karikomi, Michinori
机构
[1] Utsunomiya Univ, Grad Sch Engn, Dept Mat & Environm Chem, Utsunomiya, Tochigi 3218585, Japan
[2] Shahjalal Univ Sci & Technol, Sch Phys Sci, Dept Chem, Sylhet 3114, Bangladesh
关键词
Helicene; Furan; Cyclization; Nucleophile; Oxahelicene;
D O I
10.3987/COM-12-12640
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The reaction of helical quinone with thiols in the presence of acid such as HCl, para-toluene sulfonic acid (pTSA), or Yb(OTf)(3)center dot 3H(2)O to form resulted in the formation of thioalkoxy-substituted oxa[9]helicenes in moderate to good yields.
引用
收藏
页码:547 / 550
页数:4
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共 5 条
  • [1] Novel synthesis of a unique helical quinone derivative by coupling reaction of 2-hydroxybenzo[c]phenanthrene
    Karikomi, M
    Yamada, M
    Ogawa, Y
    Houjou, H
    Seki, K
    Hiratani, K
    Haga, K
    Uyehara, T
    [J]. TETRAHEDRON LETTERS, 2005, 46 (35) : 5867 - 5869
  • [2] Novel synthesis of alkoxy substituted oxa[9]helicenes by the reaction of helical quinone with alcohols
    Salim, Mohammad
    Ubukata, Hidenori
    Kimura, Takao
    Karikomi, Michinori
    [J]. TETRAHEDRON LETTERS, 2011, 52 (49) : 6591 - 6593
  • [3] Novel synthesis of oxa[9]helicenes by Lawesson's reagent-mediated cyclization of helical quinone derivatives
    Salim, Mohammad
    Akutsu, Akira
    Kimura, Takao
    Minabe, Masahiro
    Karikomi, Michinori
    [J]. TETRAHEDRON LETTERS, 2011, 52 (35) : 4518 - 4520
  • [4] Helicenes: Synthesis and Applications
    Shen, Yun
    Chen, Chuan-Feng
    [J]. CHEMICAL REVIEWS, 2012, 112 (03) : 1463 - 1535
  • [5] Recent developments in the synthesis of helicene-like molecules
    Urbano, A
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (34) : 3986 - 3989