Iodine-catalyzed aerobic oxidative formal [4+2] annulation for the construction of polyfunctionalized pyridines

被引：17
|
作者：
Zhu, Chunyin [1 ]
Bi, Benwei [1 ]
Ding, Ya [1 ]
Zhang, Te [1 ]
Chen, Qiu-Yun [1 ]
机构：
[1] Jiangsu Univ, Sch Chem & Chem Engn, Zhenjiang 212013, Peoples R China
来源：
TETRAHEDRON | 2015年 / 71卷 / 49期
基金：
中国国家自然科学基金;
关键词：
Iodine; 4+2] Annulation; Pyridine; Aerobic; METAL-FREE; 2+2+2 CYCLOADDITION; C-H; METHYL KETONES; MULTICOMPONENT REACTIONS; 3-COMPONENT CYCLIZATION; COUPLING REACTIONS; OXIDANT; AMINES; CYCLOTRIMERIZATION;
D O I：
10.1016/j.tet.2015.10.040
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
An iodine-catalyzed aerobic oxidative formal [4+2] annulation for the construction of polyfunctionalized pyridines in one step has been developed through the green reaction system of catalytic amounts of molecular iodine and amine in combination with oxygen. Various ketones and aldehydes were able to react with different chalcones and beta, gamma-unsaturated alpha-ketoesters through this reaction strategy. Synthetically, this iodine catalytic system could be scaled up with good efficiency. (C) 2015 Elsevier Ltd. All rights reserved.
引用
收藏
页码：9251 / 9257
页数：7
相关论文
共 50 条
  • [1] Iodine-catalyzed aerobic oxidative formal [4+2] annulation for the construction of polyfunctionalized pyridines (vol 71, pg 9251, 2015)
    Zhu, Chunyin
    Bi, Benwei
    Ding, Ya
    Zhang, Te
    Chen, Qiu-Yun
    TETRAHEDRON, 2016, 72 (05) : 779 - 779
  • [2] Iodine-Catalyzed Radical Oxidative Annulation for the Construction of Dihydrofurans and Indolizines
    Tang, Shan
    Liu, Kun
    Long, Yue
    Gao, Xinlong
    Gao, Meng
    Lei, Aiwen
    ORGANIC LETTERS, 2015, 17 (10) : 2404 - 2407
  • [3] Iodine-Catalyzed Regioselective Synthesis of Diphenyl-Substituted Carbazoles via [4+2] Annulation of β-Formyl Ketones with Indoles
    Suresh, Sundaram
    Chien, Hung-Sheng
    Chen, Chao-Hua
    Tsai, Hao-Yu
    Chung, Dai-Ru
    Kavala, Veerababurao
    Yao, Ching-Fa
    JOURNAL OF ORGANIC CHEMISTRY, 2023, 88 (24): : 17505 - 17510
  • [4] Iodine-catalyzed oxidative cyclizations for the construction of thienocarbazole derivatives
    Kivrak, Arif
    Koca, Halil
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2017, 254
  • [5] Copper(I)-Catalyzed [4+2] Oxidative Annulation of α,β-Unsaturated Ketoxime Acetates with Cyclopropanols toward Functional Pyridines
    Wu, Qinghuan
    Xu, Gaochen
    Li, Yuguang
    Shen, Lei
    Fang, Zheng
    Duan, Jindian
    Guo, Kai
    ADVANCED SYNTHESIS & CATALYSIS, 2023, 365 (23) : 4310 - 4316
  • [6] Iodine-Catalyzed Double [4+2] Oxidative Annulations for the Synthesis of Bipyrazines from Ketones and Diamines by a Domino Strategy
    Ding, Yuxin
    Zhang, Ruiqin
    Ma, Renchao
    Ma, Yongmin
    ADVANCED SYNTHESIS & CATALYSIS, 2022, 364 (02) : 355 - 361
  • [7] IODINE-CATALYZED REARRANGEMENT OF POLYFLUORINATED 2-(DICHLOROAMINO)PYRIDINES
    BANKS, RE
    BARLOW, MG
    HORNBY, JC
    MAMAGHANI, M
    JOURNAL OF FLUORINE CHEMISTRY, 1979, 14 (02) : 183 - 187
  • [8] Copper-Catalyzed Formal [4+2] Annulation between Alkyne and Fullerene Bromide
    Xiao, Zuo
    Matsuo, Yutaka
    Nakamura, Eiichi
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (35) : 12234 - 12236
  • [9] Iodine-catalyzed ultrasound-assisted construction of pyridines and their glutamine synthetase molecular docking
    Pagadala, Ramakanth
    Kasi, Venkatesan
    Perugu, Shyam
    JOURNAL OF THE CHINESE CHEMICAL SOCIETY, 2020, 67 (07) : 1296 - 1302
  • [10] Iodine-Catalyzed Aerobic Oxidative Cleavage of C-C δ-Bonds: Difunctionalization of Dienones
    Feng, Kai-Xiang
    Shen, Qiao-Yu
    Xia, Ai-Bao
    Zhang, Xing
    Huang, Li-Sha
    Xu, Zhong-Yang
    Zhou, Zhan-Yu
    Xu, Dan-Qian
    Du, Xiao-Hua
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2020, 2020 (35) : 5735 - 5740
12345