Synthesis of 2,3-disubstituted indoles by a rhodium-catalyzed aromatic amino-Claisen rearrangement of N-propargyl anilines

被引:63
|
作者
Saito, Akio [1 ]
Kanno, Ayumi [1 ]
Hanzawa, Yuji [1 ]
机构
[1] Showa Pharmaceut Univ, Lab Organ React Chem, Machida, Tokyo 1948543, Japan
关键词
alkynes; cyclization; heterocycles; rearrangement; rhodium;
D O I
10.1002/anie.200605162
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
(Chemical Equation Presented) Give me a ring! A cationic RhI catalyst promotes the formation of fused arenes containing a five-membered ring (see scheme) by an aromatic amino-Claisen rearrangement of N-propargyl aniline derivatives in refluxing hexafluoro-2-propanol (HFIP). cod = 1,5-cyclooctadiene, dppp = 1,3-bis(diphenylphosphanyl)propane, Tf = trifluoromethanesulfonyl. © 2007 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码:3931 / 3933
页数:3
相关论文
共 50 条
  • [1] Synthesis of Pyrroles by Gold(I)-Catalyzed Amino-Claisen Rearrangement of N-Propargyl Enaminone Derivatives
    Saito, Akio
    Konishi, Tomoyo
    Hanzawa, Yuji
    ORGANIC LETTERS, 2010, 12 (02) : 372 - 374
  • [2] Rhodium(I)-Catalyzed Synthesis of Indoles: Amino-Claisen Rearrangement of N-Propargylanilines
    Saito, Akio
    Oda, Shoko
    Fukaya, Haruhiko
    Hanzawa, Yuji
    JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (04): : 1517 - 1524
  • [3] Rhodium-Catalyzed Synthesis of 2,3-Disubstituted Indoles from α,β-Disubstituted Stryryl Azides
    Sun, Ke
    Liu, Sheng
    Bec, Patryk M.
    Driver, Tom G.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (07) : 1702 - 1706
  • [4] A convenient method for the aromatic amino-Claisen rearrangement of N(1,1-disubstituted-allyl)anilines
    Cooper, MA
    Lucas, MA
    Taylor, JM
    Ward, AD
    Williamson, NM
    SYNTHESIS-STUTTGART, 2001, (04): : 621 - 625
  • [5] A convenient method for the aromatic amino-claisen rearrangement of N-(1,1-disubstituted-allyl)anilines
    Cooper, M.A.
    Lucas, M.A.
    Taylor, J.M.
    Ward, A.D.
    Williamson, N.M.
    Synthesis, 2001, (04) : 621 - 625
  • [6] Copper-catalyzed synthesis of 2,3-disubstituted Indoles
    Tanimori, Shinji
    Ura, Haruna
    Kirihatali, Mitsunori
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2007, 2007 (24) : 3977 - 3980
  • [7] Use of the Ireland-Claisen rearrangement in the synthesis of 2,3-disubstituted succinates
    Pratt, LM
    Bowles, SA
    Courtney, SF
    Hidden, C
    Lewis, CN
    Martin, FM
    Todd, RS
    SYNLETT, 1998, (05) : 531 - +
  • [8] Copper-catalyzed [3+2] annulation of propargylic acetates with anilines in the presence of trimethylsilyl chloride leading to 2,3-disubstituted indoles via an aza-Claisen rearrangement
    Sakai, Norio
    Enomoto, Kota
    Takayanagi, Mitsumasa
    Konakahara, Takeo
    Ogiwara, Yohei
    TETRAHEDRON LETTERS, 2016, 57 (20) : 2175 - 2178
  • [9] A practical one-pot synthesis of 2,3-disubstituted indoles from unactivated anilines
    Tokunaga, M
    Ota, M
    Haga, MA
    Wakatsuki, Y
    TETRAHEDRON LETTERS, 2001, 42 (23) : 3865 - 3868
  • [10] INTRAMOLECULAR AROMATIC-SUBSTITUTION AND AMINO-CLAISEN REARRANGEMENT IN SUBSTITUTED N-(2-PROPYNYL)ANILINES ON ELECTRON-IMPACT
    RAMANA, DV
    SUDHA, MS
    JOURNAL OF MASS SPECTROMETRY, 1995, 30 (07): : 1028 - 1033