Potassium tert-Butoxide-Mediated Ring-Opening of Indolines: Concise Synthesis of 2-Vinylanilines

被引:0
作者
Tokushige, Keisuke [1 ]
Asai, Shota [2 ]
Abe, Takumi [1 ]
机构
[1] Okayama Univ, Grad Sch Med Dent & Pharmaceut Sci, 1-1-1 Tsushima Naka,Kita Ku, Okayama 7008530, Japan
[2] Shujitsu Univ, Sch Pharm, 1-6-1 Nishigawara,Naka Ku, Okayama 7038516, Japan
关键词
2-vinylanilines; indolines; Potassium <italic>tert</italic>-butoxide; Elimination; Ring-opening; C-H AMINATION; CATALYZED AMINATION; OLEFIN-METATHESIS; ENANTIOSELECTIVE SYNTHESIS; ARYL CHLORIDES; INDOLES; CYCLIZATION; ANILINES; CASCADE; AMMONIA;
D O I
10.1002/ajoc.202400552
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A concise and metal-free procedure has been developed for the synthesis of 2-vinylanilines. Reactions of indolines with tert-BuOK in DMSO afford the decorated 2-vinylanilines in yields up to 92 %. In addition, the 2, or 3-substituted indolines could be converted to trisubstituted alkenes. Also, the protocol can be scaled to afford gram quantities of the decorated 2-vinylanilines.
引用
收藏
页数:6
相关论文
共 102 条
  • [11] Metal-Free Coupling of 2-Vinylphenols and Carboxylic Acids: An Access to 3-Acyloxy-2,3-dihydrobenzofurans
    Chen, Jijun
    Shao, Ying
    Zheng, Hao
    Cheng, Jiang
    Wan, Xiaobing
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (21) : 10734 - 10741
  • [12] Cu(OAc)2-Promoted Cascade Carboamination/Oxidative Cyclization of C-Acylimines with Alkenes
    Dang, Ling
    Liang, Libo
    Qian, Cheng
    Fu, Meiqin
    Ma, Tongmei
    Xu, Dingguo
    Jiang, Huanfeng
    Zeng, Wei
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (02) : 769 - 776
  • [13] A Unified Approach to the Four Azaindoline Families by Inter-/Intramolecular Annulative Diamination of Vinylpyridines
    Danneman, Michael W.
    Hong, Ki Bum
    Johnston, Jeffrey N.
    [J]. ORGANIC LETTERS, 2015, 17 (15) : 3806 - 3809
  • [14] Discovery of 5-trifluoromethyl-2-aminopyrimidine derivatives as potent dual inhibitors of FLT3 and CHK1
    Deng, Minjie
    Gao, Yue
    Wang, Peipei
    Du, Wenjing
    Xu, Gaoya
    Li, Jia
    Zhou, Yubo
    Liu, Tao
    [J]. RSC MEDICINAL CHEMISTRY, 2024, 15 (02): : 539 - 552
  • [15] Enantioselective synthesis of cyclic secondary amines through Mo-catalyzed asymmetric ring-closing metathesis (ARCM)
    Dolman, SJ
    Schrock, RR
    Hoveyda, AH
    [J]. ORGANIC LETTERS, 2003, 5 (25) : 4899 - 4902
  • [16] Domnguez G., 2002, HELV CHIM ACTA, V87, P2856
  • [17] Doraghi F., 2024, J HETEROCYCLIC CHEM, V1, P1
  • [18] PALLADIUM-CATALYZED COUPLING OF ARYL TRIFLATES WITH ORGANOSTANNANES
    ECHAVARREN, AM
    STILLE, JK
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (18) : 5478 - 5486
  • [19] Synthesis of 2-Quinolinones via a Hypervalent Iodine(III)-Mediated Intramolecular Decarboxylative Heck-Type Reaction at Room Temperature
    Fan, Huaqiang
    Pang, Peng
    Zhang, Yongqiang
    Wang, Wei
    [J]. ORGANIC LETTERS, 2018, 20 (24) : 7929 - 7932
  • [20] Synthesis of 2(1H)-Quinolinones via Pd-Catalyzed Oxidative Cyclocarbonylation of 2-Vinylanilines
    Ferguson, Jamie
    Zeng, Fanlong
    Alwis, Natacha
    Alper, Howard
    [J]. ORGANIC LETTERS, 2013, 15 (08) : 1998 - 2001