Copper-Catalyzed Selective Benzylic C-O Cyclization of N-o-Tolylbenzamides: Synthesis of 4H-3,1-Benzoxazines

被引：46
|
作者：
Li, Yan [1 ,2 ]
Li, Zhongshu [2 ]
Xiong, Tao [1 ]
Zhang, Qian [1 ]
Zhang, Xiangyang [2 ]
机构：
[1] NE Normal Univ, Dept Chem, Changchun 130024, Peoples R China
[2] ETH, Organ Chem Lab, CH-8093 Zurich, Switzerland
来源：
ORGANIC LETTERS | 2012年 / 14卷 / 13期
关键词：
H BOND ACTIVATION; DIRECT ARYLATION; FUNCTIONALIZATION; AMIDATION; EFFICIENT; AMINATION; ADJACENT; INDOLES; COMPLEX; ARENES;
D O I：
10.1021/ol301492d
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A novel Selectfluor-mediated copper-catalyzed highly selective benzylic C-O cyclization for the synthesis 4H-3,1-benzoxazines is reported. The predominant selectivity for a benzylic C(sp(3))-H over an aromatic C(sp(2))-H bond in N-o-tolylbenzamides is achieved.
引用
收藏
页码：3522 / 3525
页数：4
相关论文
共 50 条
  • [21] Copper-catalyzed C-O bond cleavage and cyclization: synthesis of indazolo[3,2-b]quinazolinones
    Qiao, Rui
    Ye, Leping
    Hu, Kun
    Yu, Shuling
    Yang, Weiguang
    Liu, Miaochang
    Chen, Jiuxi
    Ding, Jinchang
    Wu, Huayue
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2017, 15 (10)
  • [22] Synthesis of 2-amino-4H-3,1-benzoxazines and 2-amino-4H-3,1-benzothiazines by the rearrangement of o-cyclopropylphenyl-ureas and o-cyclopropylphenylthioureas
    Fedotov, A. N.
    Trofimova, E. V.
    Romanov, V. A.
    Mochalov, S. S.
    Shabarov, Yu. S.
    Zefirov, N. S.
    CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2008, 44 (01) : 96 - 105
  • [23] Contribution to the Mechanism of Copper-Catalyzed C-N and C-O Bond Formation
    Lefevre, Guillaume
    Franc, Gregory
    Tlili, Anis
    Adamo, Carlo
    Taillefer, Marc
    Ciofini, Ilaria
    Jutand, Anny
    ORGANOMETALLICS, 2012, 31 (22) : 7694 - 7707
  • [24] Chiral Lewis Base Catalyzed Enantioselective Selenocyclization of 1,1-Disubstituted Alkenes: Asymmetric Synthesis of Selenium-Containing 4H-3,1-Benzoxazines
    Cao, Ren-Fei
    Yu, Lu
    Huo, Yu-Xuan
    Li, Yao
    Xue, Xiao-Song
    Chen, Zhi-Min
    ORGANIC LETTERS, 2022, 24 (22) : 4093 - 4098
  • [25] Exploiting the dual reactivity of o-isocyanobenzamide:: Three-component synthesis of 4-imino-4H-3,1-benzoxazines
    Bonne, D
    Dekhane, M
    Zhu, JP
    ORGANIC LETTERS, 2005, 7 (23) : 5285 - 5288
  • [26] Copper catalyzed C-N bond formation/C-H activation: synthesis of aryl 4H-3,1-benzoxazin-4-ones
    Munusamy, Sathishkumar
    Venkatesan, Sathesh
    Sathiyanarayanan, Kulathu Iyer
    TETRAHEDRON LETTERS, 2015, 56 (01) : 203 - 205
  • [27] Copper-Catalyzed C-N, C-O Coupling Reaction of Arylglyoxylic Acids with Isatins
    Prakash, Rashmi
    Gogoi, Sanjib
    ADVANCED SYNTHESIS & CATALYSIS, 2016, 358 (19) : 3046 - 3049
  • [28] Copper-catalyzed selective C-O bond formation by oxidative α-C(sp3)-H/O-H coupling between ethers and salicylaldehydes
    Barve, Balaji D.
    Wu, Yang-Chang
    El-Shazly, Mohamed
    Korinek, Michal
    Cheng, Yuan-Bin
    Wang, Jeh-Jeng
    Chang, Fang-Rong
    TETRAHEDRON, 2015, 71 (15) : 2290 - 2297
  • [29] SYNTHESIS OF 2-ARYL-(Z)-4-(HALOMETHYLIDENE)-4H-3,1-BENZOXAZINES BY SODIUM HYDRIDE MEDIATED CYCLIZATION OF N-[2-(2,2-DIHALOETHENYL)PHENYL]ARENECARBOXAMIDES
    Kobayashi, Kazuhiro
    Nozawa, Ippei
    Kado, Daiki
    HETEROCYCLES, 2014, 89 (12) : 2729 - 2738
  • [30] Synthesis of 4H-3,1-benzoxazines, quinazolin-2-ones, and quinoline-4-ones by palladium-catalyzed oxidative carbonylation of 2-ethynylaniline derivatives
    Costa, M
    Della Cà, N
    Gabriele, B
    Massera, C
    Salerno, G
    Soliani, M
    JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (07): : 2469 - 2477
12345