Copper-Catalyzed Domino Synthesis of Quinazolinones via Ullmann-Type Coupling and Aerobic Oxidative C-H Amidation

被引:227
|
作者
Xu, Wei [1 ]
Jin, Yibao [2 ]
Liu, Hongxia [2 ]
Jiang, Yuyang [2 ]
Fu, Hua [1 ]
机构
[1] Tsinghua Univ, Dept Chem, Key Lab Bioorgan Phosphorus Chem & Chem Biol Mini, Beijing 100084, Peoples R China
[2] Tsinghua Univ, Grad Sch Shenzhen, Key Lab Chem Biol Guangdong Prov, Shenzhen 518057, Peoples R China
基金
中国国家自然科学基金;
关键词
ARYL HALIDES; EFFICIENT SYNTHESIS; N-ARYLATION; DERIVATIVES; LIGAND; AMINES; ALKALOIDS; CHEMISTRY; NITROGEN; AMIDES;
D O I
10.1021/ol1030266
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An efficient copper-catalyzed approach to quinazolinone derivatives has been developed, and the protocol uses cheap and readily available substituted 2-halobenzamides and (aryl)methanamines as the starting materials as well as economical and environmentally friendly air as the oxidant. This can be the first example of constructing N-heterocycles via sequential Ullmann-type coupling under air and aerobic oxidative C-H amidation.
引用
收藏
页码:1274 / 1277
页数:4
相关论文
共 50 条
  • [41] Copper-Catalyzed Aerobic Aliphatic C-H Oxygenation Directed by an Amidine Moiety
    Wang, Yi-Feng
    Chen, Hui
    Zhu, Xu
    Chiba, Shunsuke
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (29) : 11980 - 11983
  • [42] 1-(Hydroxymethyl)-1H-benzotriazole: An Efficient Ligand for Copper-Catalyzed Ullmann-Type Coupling Reaction Leading to Expeditious Synthesis of Diverse Benzoxazoles and Benzothiazoles
    Singh, Mala
    Bose, Priyanka
    Singh, Anoop S.
    Tiwari, Vinod K.
    CHEMISTRYSELECT, 2019, 4 (33): : 9627 - 9631
  • [43] TBAI-catalyzed synthesis of α-ketoamides via sp3 C-H radical/radical cross-coupling and domino aerobic oxidation
    Fan, Weizheng
    Shi, Dongyang
    Feng, Bainian
    TETRAHEDRON LETTERS, 2015, 56 (31) : 4638 - 4641
  • [44] Copper-Catalyzed Aerobic Methyl/Methylene Oxygenation and C-H Formylation with a DABCO-DMSO System for the Synthesis of Carbonyl Indoles and Pyrroles
    Wang, Yi-Feng
    Zhang, Feng-Lian
    Chiba, Shunsuke
    SYNTHESIS-STUTTGART, 2012, 44 (10): : 1526 - 1534
  • [45] Copper-Catalyzed Oxidative Multicomponent Annulation Reaction for Direct Synthesis of Quinazolinones via an Imine-Protection Strategy
    Liang, Yantang
    Tan, Zhenda
    Jiang, Huanfeng
    Zhu, Zhibo
    Zhang, Min
    ORGANIC LETTERS, 2019, 21 (12) : 4725 - 4728
  • [46] Microwave-Assisted, Copper-Catalyzed Domino O-H/C-H Arylation Reaction toward the Synthesis of Oxygen-Doped Polyaromatic Molecules
    Kaplanai, Entzy
    Tonis, Efstathios
    Drymona, Maria
    Zagranyarski, Yulian
    Tzeli, Demeter
    Vougioukalakis, Georgios C.
    JOURNAL OF ORGANIC CHEMISTRY, 2023, 88 (16): : 11552 - 11561
  • [47] Copper-catalyzed aerobic decarboxylative coupling between cyclic α-amino acids and diverse C-H nucleophiles with low catalyst loading
    Guo, Jing
    Xie, Ying
    Wu, Qiao-Lei
    Zeng, Wen-Tian
    Chan, Albert S. C.
    Weng, Jiang
    Lu, Gui
    RSC ADVANCES, 2018, 8 (29): : 16202 - 16206
  • [48] Ligand-Free, Copper-Catalyzed Ullmann-Type C-N Coupling: Regioselective Synthesis of Azole-Substituted Imidazo[1,2-a]pyridines
    Kaswan, Pinku
    Pericherla, Kasiviswanadharaju
    Kumar, Anil
    SYNLETT, 2013, 24 (20) : 2751 - 2757
  • [49] Copper-Catalyzed Intramolecular C-H Amination
    Barman, Dipti N.
    Nicholas, Kenneth M.
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2011, 2011 (05) : 908 - 911
  • [50] Copper-Catalyzed C-H Alkoxylation of Azoles
    Takemura, Noriaki
    Kuninobu, Yoichiro
    Kanai, Motomu
    ORGANIC LETTERS, 2013, 15 (04) : 844 - 847