Zinc-promoted hydrohydrazination of terminal alkynes: An efficient domino synthesis of indoles

被引:152
|
作者
Alex, Karolin [1 ]
Tillack, Annegret [1 ]
Schwarz, Nicolle [1 ]
Beller, Matthias [1 ]
机构
[1] Univ Rostock, Leibniz Inst Katalyse eV, D-18059 Rostock, Germany
关键词
alkynes; hydrohydrazinations; indole; zinc;
D O I
10.1002/anie.200703823
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
(Chemical Equation Presented) Indole click chemistry: The quest for better catalysts for the intermolecular hydrohydrazination to indoles leads to zinc salts. A simple one-pot synthesis forms indoles from arylhydrazines and terminal alkynes. The pharmacologically relevant indole building blocks are selectively formed in the presence of zinc triflate (Zn(OTf)2) or ZnCl 2 (see scheme). © 2008 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码:2304 / 2307
页数:4
相关论文
共 50 条
  • [1] One-Pot Synthesis of Polysubstituted Indoles via the Indium-Promoted Regioselective Hydrohydrazination of Terminal Alkynes
    Sakai, Norio
    Yokoyama, Takahiro
    Ishida, Kento
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2025, 14 (03)
  • [2] Zinc-Chloride-Promoted Domino Reaction of Phenols with Terminal Alkynes under Solvent-Free Conditions: An Efficient Synthesis of Chromenes
    Sreenivasulu, Chinnabattigalla
    Satyanarayana, Gedu
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2018, 2018 (22) : 2846 - 2857
  • [3] A facile and efficient zinc-promoted allylation of carbonyl compounds
    Chen, CP
    Dai, WC
    Chang, HG
    ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL, 2002, 34 (05) : 507 - 511
  • [4] ZINC-PROMOTED RANEY COPPER-CATALYSTS FOR METHANOL SYNTHESIS
    MARSDEN, WL
    WAINWRIGHT, MS
    FRIEDRICH, JB
    INDUSTRIAL & ENGINEERING CHEMISTRY PRODUCT RESEARCH AND DEVELOPMENT, 1980, 19 (04): : 551 - 556
  • [5] The first zinc-promoted, environmentally friendly, and highly efficient acetoxyallylation of aldehydes in aqueous ammonium chloride
    Lombardo, M
    Girotti, R
    Morganti, S
    Trombini, C
    CHEMICAL COMMUNICATIONS, 2001, (22) : 2310 - 2311
  • [6] Efficient synthesis of multiply substituted butenolides from keto acids and terminal alkynes promoted by combined acids
    Mao, Wenbin
    Zhu, Chen
    ORGANIC CHEMISTRY FRONTIERS, 2017, 4 (06): : 1029 - 1033
  • [7] Catalytic synthesis of dihydropyridines by domino reaction of terminal alkynes, carbodiimides, and acetylenic esters
    Jalali, Mozhgan Sadat
    Manafi, Mohammadreza
    Homami, Seyed Saied
    Gorji, Banafsheh
    Monzavi, Amirhossein
    MONATSHEFTE FUR CHEMIE, 2020, 151 (07): : 1173 - 1181
  • [8] Catalytic synthesis of dihydropyridines by domino reaction of terminal alkynes, carbodiimides, and acetylenic esters
    Mozhgan Sadat Jalali
    Mohammadreza Manafi
    Seyed Saied Homami
    Banafsheh Gorji
    Amirhossein Monzavi
    Monatshefte für Chemie - Chemical Monthly, 2020, 151 : 1173 - 1181
  • [9] 3-Bromo-propenyl acetate in organic synthesis.: The zinc-promoted α-hydroxyallylation of ketones
    Lombardo, M
    Morganti, S
    d'Ambrosio, F
    Trombini, C
    TETRAHEDRON LETTERS, 2003, 44 (14) : 2823 - 2826
  • [10] Synthesis of 2-Boryl Allylboronates by a Bimetallic Platinum/Zinc-Promoted Diborylation of Propargylic Amines
    Shi, Xiao-Nan
    Wang, Jia-Le
    Wu, Jiang-Bin
    Zhuo, Chun-Xiang
    SYNLETT, 2023, 34 (13) : 1573 - 1576