Multicomponent approach to the synthesis of oxidized amides through nitrile hydrozirconation

被引：47
|
作者：
Wan, Shuangyi [1 ]
Green, Michael E. [1 ]
Park, Jung-Hyun [1 ]
Floreancig, Paul E. [1 ]
机构：
[1] Univ Pittsburgh, Dept Chem, Pittsburgh, PA 15260 USA
来源：
ORGANIC LETTERS | 2007年 / 9卷 / 26期
关键词：
D O I：
10.1021/ol702184n
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Oxidized amides, as represented by acyl aminals and acyl hemiaminals, are integral subunits of several natural products that exhibit useful biological activity. In this paper a multicomponent approach to these groups from acylimine intermediates is demonstrated. The acylimines; are accessed through a sequence of nitrile hydrozirconation and acylation, making this highly versatile amide synthesis useful for a range of applications in target- and diversity-oriented synthesis.
引用
收藏
页码：5385 / 5388
页数：4
相关论文
共 50 条
  • [1] Stereoselective Synthesis of Spirooxindole Amides through Nitrile Hydrozirconation
    Lu, Chunliang
    Xiao, Qing
    Floreancig, Paul E.
    ORGANIC LETTERS, 2010, 12 (22) : 5112 - 5115
  • [2] Multicomponent Synthesis of α-Branched Amides
    DeBenedetto, Mikkel V.
    Green, Michael E.
    Wan, Shuangyi
    Park, Jung-Hyun
    Floreancig, Paul E.
    ORGANIC LETTERS, 2009, 11 (04) : 835 - 838
  • [3] SYNTHESIS OF ENAMIDES AND AMIDES BY HYDROZIRCONATION-ACYLATION OF SCHIFF-BASES
    NG, KS
    LAYCOCK, DE
    ALPER, H
    JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (14): : 2899 - 2901
  • [4] A New Multicomponent Reaction for the Synthesis of Amides
    Fekri, Leila Zare
    Farjood, Marjan
    ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL, 2021, 53 (03) : 291 - 300
  • [5] Construction of a Spirooxindole Amide Library through Nitrile Hydrozirconation-Acylation-Cyclization Cascade
    LaPorte, Matthew G.
    Tsegay, Sammi
    Hong, Ki Bum
    Lu, Chunliang
    Fang, Cheng
    Wang, Lirong
    Xie, Xiang-Qun
    Floreancig, Paul E.
    ACS COMBINATORIAL SCIENCE, 2013, 15 (07) : 344 - 349
  • [6] A Multicomponent Approach to Oxazolidinone Synthesis Catalyzed by Rare-Earth Metal Amides
    Zhou, Meixia
    Zheng, Xizhou
    Wang, Yaorong
    Yuan, Dan
    Yao, Yingming
    CHEMCATCHEM, 2019, 11 (23) : 5783 - 5787
  • [7] Multicomponent Approach to Libraries of Substituted Dihydroorotic Acid Amides
    Bellucci, Maria Cristina
    Sacchetti, Alessandro
    Volonterio, Alessandro
    ACS COMBINATORIAL SCIENCE, 2019, 21 (10) : 705 - 715
  • [8] NITRILE SYNTHESIS - DEHYDRATION OF AMIDES BY SILAZANES, CHLOROSILANES, ALKOXYSILANES, AND AMINOSILANES
    DENNIS, WE
    JOURNAL OF ORGANIC CHEMISTRY, 1970, 35 (10): : 3253 - &
  • [9] Multifaceted catalysis approach to nitrile activation: direct synthesis of halogenated allyl amides from allylic alcohols
    Lester, Roy P.
    Dunsford, Jay J.
    Camp, Jason E.
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2013, 11 (43) : 7472 - 7476
  • [10] One-Pot Multicomponent Synthesis of β-Amino Amides
    Huang, Bo
    Zeng, Linwei
    Shen, Yangyong
    Cui, Sunliang
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (16) : 4565 - 4568
12345