3-(Triflyloxy)benzynes Enable the Regiocontrolled Cycloaddition of Cyclic Ureas to Synthesize 1,4-Benzodiazepine Derivatives

被引:14
作者
Kaneko, Hideki [1 ]
Ikawa, Takashi [1 ]
Yamamoto, Yuta [2 ]
Arulmozhiraja, Sundaram [2 ]
Tokiwa, Hiroaki [2 ]
Akai, Shuji [1 ]
机构
[1] Osaka Univ, Grad Sch Pharmaceut Sci, 1-6 Yamadaoka, Suita, Osaka 5650871, Japan
[2] Rikkyo Univ, Dept Chem, Res Ctr Smart Mol, Toshima Ku, 3-34-1 Nishi Ikebukuro, Tokyo 1718501, Japan
关键词
benzodiazepines; benzynes; triflyloxy group; imidazolidinones; regioselectivity; directing group; REGIOSELECTIVE DIELS-ALDER; SELECTIVE SYNTHESIS; ARYNE; GENERATION; CONSTRUCTION; BENZODIAZEPINE; CHEMISTRY; BORYL;
D O I
10.1055/s-0036-1591924
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A versatile synthesis of 1,4-benzodiazepine derivatives through the reaction of various 3-(trifluoromethanesulfonyloxy)benzynes with N-(p-toluenesulfonyl) imidazolidin-2-ones is reported. This reaction system provides a 1,4-benzodiazepine bearing a trifluoromethanesulfonyloxy group as a single regioisomer among the four possible regioisomers.
引用
收藏
页码:943 / +
页数:7
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共 34 条
  • [1] Synthesis of biaryl compounds through three-component assembly:: Ambidentate effect of the tert-butyldimethylsilyl group for regioselective Diels-Alder and Hiyama coupling reactions
    Akai, Shuji
    Ikawa, Takashi
    Takayanagi, Sho-ichi
    Morikawa, Yuki
    Mohri, Shinya
    Tsubakiyama, Masaya
    Egi, Masahiro
    Wada, Yasufami
    Kita, Yasuyuki
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (40) : 7673 - 7676
  • [2] New Synthetic Routes to Triazolo-benzodiazepine Analogues: Expanding the Scope of the Bump-and-Hole Approach for Selective Bromo and Extra-Terminal (BET) Bromodomain Inhibition
    Baud, Matthias G. J.
    Lin-Shiao, Enrique
    Zengerle, Michael
    Tallant, Cynthia
    Ciulli, Alessio
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 2016, 59 (04) : 1492 - 1500
  • [3] Steric Effects Compete with Aryne Distortion To Control Regioselectivities of Nucleophilic Additions to 3-Silylarynes
    Bronner, Sarah M.
    Mackey, Joel L.
    Houk, K. N.
    Garg, Neil K.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (34) : 13966 - 13969
  • [4] An Atom-Economical Method To Prepare Enantiopure Benzodiazepines with N-Carboxyanhydrides
    Fier, Patrick S.
    Whittaker, Aaron M.
    [J]. ORGANIC LETTERS, 2017, 19 (06) : 1454 - 1457
  • [5] Goetz AE, 2013, NAT CHEM, V5, P54, DOI [10.1038/NCHEM.1504, 10.1038/nchem.1504]
  • [6] Synthesis of Optically Active 2,3-Disubstituted Indoline Derivatives through Cycloaddition Reactions between Benzynes and α,β-Unsaturated γ-Aminobutyronitriles
    Ikawa, Takashi
    Sumii, Yuta
    Masuda, Shigeaki
    Wang, Ding
    Emi, Yuto
    Takagi, Akira
    Akai, Shuji
    [J]. SYNLETT, 2018, 29 (04) : 530 - 536
  • [7] 1,3-and 1,4-Benzdiyne equivalents for regioselective synthesis of polycyclic heterocycles
    Ikawa, Takashi
    Masuda, Shigeaki
    Takagi, Akira
    Akai, Shuji
    [J]. CHEMICAL SCIENCE, 2016, 7 (08) : 5206 - 5211
  • [8] Trifluoromethanesulfonyloxy-group-directed regioselective (3+2) cycloadditions of benzynes for the synthesis of functionalized benzo-fused heterocycles
    Ikawa, Takashi
    Kaneko, Hideki
    Masuda, Shigeaki
    Ishitsubo, Erika
    Tokiwa, Hiroaki
    Akai, Shuji
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2015, 13 (02) : 520 - 526
  • [9] Regiocomplementary Cycloaddition Reactions of Boryl- and Silylbenzynes with 1,3-Dipoles: Selective Synthesis of Benzo-Fused Azole Derivatives
    Ikawa, Takashi
    Takagi, Akira
    Goto, Masahiko
    Aoyama, Yuya
    Ishikawa, Yoshinobu
    Itoh, Yuji
    Fujii, Satoshi
    Tokiwa, Hiroaki
    Akai, Shuji
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (07) : 2965 - 2983
  • [10] ortho-Selective Nucleophilic Addition of Primary Amines to Silylbenzynes: Synthesis of 2-Silylanilines
    Ikawa, Takashi
    Nishiyama, Tsuyoshi
    Shigeta, Takashi
    Mohri, Shinya
    Morita, Shinsuke
    Takayanagi, Sho-ichi
    Terauchi, Yuki
    Morikawa, Yuki
    Takagi, Akira
    Ishikawa, Yoshinobu
    Fujii, Satoshi
    Kita, Yasuyuki
    Akai, Shuji
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (25) : 5673 - 5676