Direct, One-pot Sequential Reductive Alkylation of Lactams/Amides with Grignard and Organolithium Reagents through Lactam/Amide Activation

被引：229
|
作者：
Xiao, Kai-Jiong [1 ,2 ]
Luo, Jie-Min [1 ,2 ]
Ye, Ke-Yin [1 ,2 ]
Wang, Yu [1 ,2 ]
Huang, Pei-Qiang [1 ,2 ]
机构：
[1] Xiamen Univ, Dept Chem, Xiamen 361005, Fujian, Peoples R China
[2] Xiamen Univ, Key Lab Chem Biol Fujian Prov, Coll Chem & Chem Engn, Xiamen 361005, Fujian, Peoples R China
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2010年 / 49卷 / 17期
关键词：
amides; multicomponent reactions; sequential reductive alkylation; synthetic methods; tert-alkylamines; FUNCTIONALIZED ARYLMAGNESIUM; PYRIDINE-DERIVATIVES; THIOIMINIUM SALTS; TRIFLIC ANHYDRIDE; TERTIARY AMIDES; VILSMEIER-HAACK; ARYL AMIDES; CASCADE; AMINES; THIOFORMAMIDES;
D O I：
10.1002/anie.201000652
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
(Figure Presented) Be dazzled by the sequence: The first efficient and general one-pot method for the reductive bisalkylation of lactams/ amides with Grignard and organolithium reagents has been developed (see scheme; DTBMP = 2,6-di-tert-butyl-4methylpyridine, Tf=trifluoromethanesulfonyl). © 2010 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码：3037 / 3040
页数：4
相关论文
共 28 条
  • [1] Versatile One-Pot Reductive Alkylation of Lactams/Amides via Amide Activation: Application to the Concise Syntheses of Bioactive Alkaloids (±)-Bgugaine, (±)-Coniine, (+)-Preussin, and (-)-Cassine
    Xiao, Kai-Jiong
    Wang, Yu
    Ye, Ke-Yin
    Huang, Pei-Qiang
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2010, 16 (43) : 12792 - 12796
  • [2] SEQUENTIAL ONE-POT REACTIONS OF THIOFORMAMIDES WITH ORGANOLITHIUM AND ZINC REAGENTS
    Murai, Toshiaki
    Matsushita, Koji
    [J]. PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2011, 186 (05) : 1094 - 1103
  • [3] Facile One-Pot Direct Arylation and Alkylation of Nitropyridine N-Oxides with Grignard Reagents
    Zhang, Fang
    Duan, Xin-Fang
    [J]. ORGANIC LETTERS, 2011, 13 (22) : 6102 - 6105
  • [4] Small-Scale One-Pot Reductive Alkylation of Unprotected Aminocyclitols with Supported Reagents
    Sisa, Miroslav
    Trapero, Ana
    Llebaria, Amadeu
    Delgado, Antonio
    [J]. SYNTHESIS-STUTTGART, 2008, (19): : 3167 - 3170
  • [5] One-pot sequential 1,2-addition, Pd-catalysed cross-coupling of organolithium reagents with Weinreb amides
    Giannerini, M.
    Vila, C.
    Hornillos, V.
    Feringa, B. L.
    [J]. CHEMICAL COMMUNICATIONS, 2016, 52 (06) : 1206 - 1209
  • [6] Synthesis of Tryptamine Derivatives via a Direct, One-Pot Reductive Alkylation of Indoles
    Righi, Marika
    Topi, Francesca
    Bartolucci, Silvia
    Bedini, Annalida
    Piersanti, Giovanni
    Spadoni, Gilberto
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (14): : 6351 - 6357
  • [7] One-Pot, Tandem Reductive Amination/Alkylation-Cycloamidation for Lactam Synthesis from Keto or Amino Acids
    Ramachandran, P. Veeraraghavan
    Choudhary, Shivani
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2023, 88 (22): : 15956 - 15963
  • [8] General One-Pot Reductive gem-Bis-Alkylation of Tertiary Lactams/Amides: Rapid Construction of 1-Azaspirocycles and Formal Total Synthesis of (±)-Cephalotaxine
    Xiao, Kai-Jiong
    Luo, Jie-Min
    Xia, Xiao-Er
    Wang, Yu
    Huang, Pei-Qiang
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2013, 19 (39) : 13075 - 13086
  • [9] Direct transformation of amides: a one-pot reductive Ugi-type three-component reaction of secondary amides
    Zheng, Jian-Feng
    Qian, Xiang-Yang
    Huang, Pei-Qiang
    [J]. ORGANIC CHEMISTRY FRONTIERS, 2015, 2 (08): : 927 - 935
  • [10] One-Pot Reductive Mono-N-alkylation of Aromatic Nitro Compounds Using Nitriles as Alkylating Reagents
    Neogi, Subhasish
    Naskar, Dinabandhu
    [J]. SYNTHETIC COMMUNICATIONS, 2011, 41 (13) : 1901 - 1915
123