Oxoarylation of ynamides with N-aryl hydroxamic acids

被引:0
|
作者
Changwei Chen [1 ]
Hongyu Zhang [2 ]
Gang Xu [2 ]
Sunliang Cui [1 ]
机构
[1] College of Pharmaceutical Sciences, Zhejiang University
[2] College of Chemical and Biological Engineering, Zhejiang University
基金
中国国家自然科学基金;
关键词
D O I
暂无
中图分类号
O621.25 [];
学科分类号
070303 ; 081704 ;
摘要
Ynamides are electron-rich alkynes with unique reactivities and act as flexible building blocks in organic synthesis.Therefore,the investigation for transformation of ynamides with exceptional selectivity and efficiency is attractive and interesting.Herein,we report an oxoarylation of ynamides with N-aryl hydroxamic acids.In the presence of catalytic Cu(OTf)2,both the terminal and internal ynamides could undergo an addition/[3,3] sigmatropic rearrangement cascade with N-aryl hydroxamic acids to achieve oxoarylation,along with providing selective entry to(ortho-amino)arylacetamides and oxindoles.Moreover,deuterium-labelling reaction and gram-scale reaction were conducted to probe the mechanism and showcase the scalability.
引用
收藏
页码:2551 / 2554
页数:4
相关论文
共 50 条
  • [21] Some N-aryl barbituric acids. III
    Buck, JS
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1937, 59 : 1249 - 1251
  • [22] Photoinduced Carbamoylarylation of Alkynes with N-Aryl Oxamic Acids
    Sekine, Kohei
    Yue, Gaofan
    Kajiwara, June
    Wu, Di
    Shiozuka, Akira
    Kuninobu, Yoichiro
    ORGANIC LETTERS, 2025,
  • [23] Visible-Light Induced and PIFA Enabled [4+2] Annulation of Alkenes with N-Aryl Substituted Hydroxamic Acids
    Wang, Yu-Zhao
    Jiang, Menglu
    Zhang, Feng
    Zhang, Hua-Wei
    Wu, Yue
    Yu, Wei
    Li, Yan
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2024, 27 (44)
  • [24] N-aryl heterocycles via coupling reactions with arylboronic acids
    Mederski, WWKR
    Lefort, M
    Germann, M
    Kux, D
    TETRAHEDRON, 1999, 55 (44) : 12757 - 12770
  • [25] A safe and selective method for reduction of 2-nitrophenylacetic acid systems to N-aryl hydroxamic acids using continuous flow hydrogenation
    Ichire, Ogar
    Jans, Petra
    Parfenov, Galina
    Dounay, Amy B.
    TETRAHEDRON LETTERS, 2017, 58 (06) : 582 - 585
  • [26] Dioxygen affinities and catalytic oxidation performance of cobalt (II)complexes with N-aryl hydroxamic acid
    Zhang, CC
    Zeng, W
    Li, JZ
    Qin, SY
    CHINESE CHEMICAL LETTERS, 2003, 14 (06) : 627 - 630
  • [28] COORDINATION-COMPOUNDS OF TIN(II) WITH SOME N-ARYL DERIVATIVES OF METHACRYL HYDROXAMIC ACID
    STRATULAT, AA
    KOORDINATSIONNAYA KHIMIYA, 1988, 14 (04): : 464 - 476
  • [29] A new route to N-aryl 2-alkenamides, N-allyl N-aryl 2-alkenamides, and N-aryl α,β-unsaturated γ-lactams from N-aryl 3-(phenylsulfonyl)propanamides
    Wang, EC
    Huang, KS
    Lin, GW
    Lin, JR
    Hsu, MK
    JOURNAL OF THE CHINESE CHEMICAL SOCIETY, 2001, 48 (01) : 83 - 90
  • [30] Efficient preparation of chiral N-aryl b-amino acids
    Hermsen, Peter
    Busscher, Guuske
    Lefort, Laurent
    de Vries, Andre
    de Vries, Hans
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2010, 240