Cascade Formation of C3-Unsymmetric Spirooxindoles via PhI(OAc)2-Mediated Oxidative C-C/C-N Bond Formation

被引：14
|
作者：
Sun, Jiyun [1 ]
Li, Guangchen [1 ]
Zhang, Guangtao [1 ]
Cong, Ying [1 ]
An, Xuechan [1 ]
Zhang-Negrerie, Daisy [1 ]
Du, Yunfei [1 ,2 ]
机构：
[1] Tianjin Univ, Sch Pharmaceut Sci & Technol, Tianjin Key Lab Modern Drug Delivery & High Effic, Tianjin 300072, Peoples R China
[2] Collaborat Innovat Ctr Chem Sci & Engn Tianjin, Tianjin 300072, Peoples R China
来源：
ADVANCED SYNTHESIS & CATALYSIS | 2018年 / 360卷 / 13期
基金：
中国国家自然科学基金;
关键词：
spirooxindole; PhI(OAc)(2); metal-free conditions; cascade reaction; oxidative coupling; METAL-FREE CONDITIONS; HYPERVALENT IODINE OXIDATION; ORGANIC-SYNTHESIS; INTRAMOLECULAR ANNULATION; ANTIMICROBIAL ACTIVITY; SYNTHETIC APPLICATIONS; H FUNCTIONALIZATION; DOMINO REACTIONS; DERIVATIVES; CONSTRUCTION;
D O I：
10.1002/adsc.201800314
中图分类号：
O69 [应用化学];
学科分类号：
081704 ;
摘要：
A series of C-3-unsymmetric spirooxindoles were achieved by reaction of diphenylmalonamides with PhI(OAc)(2) (PIDA) under metal-free conditions. Control experiments suggest that the hypervalent iodine-mediated reaction undergoes a cascade process involving an oxidative C-C bond formation preceeding an oxidative C-N bond formation.
引用
收藏
页码：2476 / 2481
页数：6
相关论文
共 50 条
  • [21] Copper-catalyzed oxidative C-H bond functionalization of N-allylbenzamide for C-N and C-C bond formation
    Ranjith, Jala
    Krishna, Palakodety Radha
    TETRAHEDRON LETTERS, 2019, 60 (21) : 1437 - 1440
  • [22] Synthesis of substituted tetrahydron-1H-carbazol-1-one and analogs via PhI(OCOCF3)2-mediated oxidative C-C bond formation
    Shi, Hao
    Guo, Tianjian
    Zhang-Negrerie, Daisy
    Du, Yunfei
    Zhao, Kang
    TETRAHEDRON, 2014, 70 (17) : 2753 - 2760
  • [23] Copper-Catalyzed Synthesis of 2-Aminocarbazoles through Cascade C-C and C-N Bond Formation and Aromatization
    Liu, Xinlei
    Huang, Jiangkun
    Xu, Huibei
    Zhang, Dandan
    Sun, Qiu
    He, Ling
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2019, 2019 (05) : 900 - 906
  • [24] CO2 activation through C-N, C-O and C-C bond formation
    Eftaiha, Ala'a F.
    Qaroush, Abdussalam K.
    Okashah, Ibrahim K.
    Alsoubani, Fatima
    Futter, Jonas
    Troll, Carsten
    Rieger, Bernhard
    Assaf, Khaleel I.
    PHYSICAL CHEMISTRY CHEMICAL PHYSICS, 2020, 22 (03) : 1306 - 1312
  • [25] Metal-Free Cascade Formation of C-C and C-N Bond for the Construction of 3-Cyano-2-Pyridones with Insecticidal Properties
    Tang, Yao
    Wu, Nvjiang
    Xu, Junyu
    Zhang, Xiaopo
    Li, Youbin
    Wang, Xuesong
    MOLECULES, 2024, 29 (12):
  • [26] NEW SYNTHETIC METHODS OF PYRAZINOISOQUINOLINES BY SIMULTANEOUS C-N AND C-C BOND FORMATION
    KIM, CS
    KIM, JH
    LEE, NJ
    HETEROCYCLES, 1984, 21 : 661 - 661
  • [27] New look of potassium allyltrifluoroborates in C-C and C-N bond formation reactions
    Al-Masum, Mohammad
    Liu, Kwei
    Ng, Eunice
    Wai, Maya
    Alam, Shahrina
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2011, 242
  • [28] Formation of organopalladium complexes via C-Br and C-C bond activation. Application in C-C and C-N coupling reactions
    Majumder, Paramita
    Paul, Piyali
    Sengupta, Poulami
    Bhattacharya, Samaresh
    JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2013, 736 : 1 - 8
  • [29] Efficient Synthesis of Pyrazoles: Oxidative C-C/N-N Bond-Formation Cascade
    Neumann, Julia J.
    Suri, Mamta
    Glorius, Frank
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (42) : 7790 - 7794
  • [30] Enzyme mediated C-C bond formation
    Fessner, WD
    CURRENT OPINION IN CHEMICAL BIOLOGY, 1998, 2 (01) : 85 - 97
12345