Manganese-Catalyzed Allylation of Quinazolinones with 4-Vinyl-1,3-dioxolan-2-one via C-H Activation

被引:2
|
作者
Li Yudong [1 ,2 ]
Li Ying [1 ]
Dong Ya'nan [1 ]
Xia Chungu [1 ]
Li Yuehui [1 ]
机构
[1] Chinese Acad Sci, Lanzhou Inst Chem Phys LICP, Suzhou Res Inst LICP, State Key Lab Oxo Synth & Select Oxidat, Lanzhou 730000, Peoples R China
[2] Univ Chinese Acad Sci, Beijing 100049, Peoples R China
基金
中国国家自然科学基金;
关键词
manganese-catalyzed; allylation; quinazolinones; C-H activation; EXPEDIENT ACCESS; BOND FORMATION; FUNCTIONALIZATION; ARYLATION; SULFAMIDATION; STRATEGIES; ALDEHYDES; IMINES;
D O I
10.6023/cjoc202110002
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The ortho-allylation of quinazolinones with 4-vinyl-1,3-dioxolan-2-one via manganese catalysis has been described. A series of allylation products with potential applications have been obtained. This protocol is also highlighted by good compatibility of functional groups and excellent E/Z selectivity. This work broadens the scope of Mn-catalyzed C-C coupling reactions.
引用
收藏
页码:847 / 853
页数:7
相关论文
共 57 条
  • [11] C-H functionalization of quinazolinones by transition metal catalysis
    Ghosh, Prasanjit
    Ganguly, Bhaskar
    Das, Sajal
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2020, 18 (24) : 4497 - 4518
  • [12] Copper-Catalyzed C-H Functionalization Reactions: Efficient Synthesis of Heterocycles
    Guo, Xun-Xiang
    Gu, Da-Wei
    Wu, Zhengxing
    Zhang, Wanbin
    [J]. CHEMICAL REVIEWS, 2015, 115 (03) : 1622 - 1651
  • [13] Mechanistic Insight into Catalytic Redox-Neutral C-H Bond Activation Involving Manganese(I) Carbonyls: Catalyst Activation, Turnover, and Deactivation Pathways Reveal an Intricate Network of Steps
    Hammarback, L. Anders
    Robinson, Alan
    Lynam, Jason M.
    Fairlamb, Ian J. S.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2019, 141 (06) : 2316 - 2328
  • [14] Palladium-Catalyzed Transformations of Alkyl C-H Bonds
    He, Jian
    Wasa, Masayuki
    Chan, Kelvin S. L.
    Shao, Ojan
    Yu, Jin-Quan
    [J]. CHEMICAL REVIEWS, 2017, 117 (13) : 8754 - 8786
  • [15] Mn-Catalyzed Three-Component Reactions of Imines/Nitriles, Grignard Reagents, and Tetrahydrofuran: An Expedient Access to 1,5-Amino/Keto Alcohols
    He, Ruoyu
    Jin, Xiqing
    Chen, Hui
    Huang, Zhi-Tang
    Zheng, Qi-Yu
    Wang, Congyang
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2014, 136 (18) : 6558 - 6561
  • [16] Manganese- Catalyzed Dehydrogenative [4+2] Annulation of N-H Imines and Alkynes by C- H/N- H Activation**
    He, Ruoyu
    Huang, Zhi-Tang
    Zheng, Qi-Yu
    Wang, Congyang
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (19) : 4950 - 4953
  • [17] Manganese-Catalyzed C-H Olefination Reactions
    Hu, Yuanyuan
    Wang, Congyang
    [J]. CHEMCATCHEM, 2019, 11 (04) : 1167 - 1174
  • [18] Manganese-Catalyzed Redox-Neutral C-H Olefination of Ketones with Unactivated Alkenes
    Hu, Yuanyuan
    Zhou, Bingwei
    Chen, Hui
    Wang, Congyang
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2018, 57 (37) : 12071 - 12075
  • [19] Manganese-catalyzed bicyclic annulations of imines and α,β-unsaturated esters via C-H activation
    Hu, Yuanyuan
    Wang, Congyang
    [J]. SCIENCE CHINA-CHEMISTRY, 2016, 59 (10) : 1301 - 1305
  • [20] Rhodium-catalyzed tandem C-H activation and aza-Michael addition of 2-arylquinazolin-4-ones with acrylates for the synthesis of pyrrolo[2,1-b]quinazolin-9(1H)-one derivatives
    Jiang, Xin
    Yang, Qin
    Yuan, Jianjun
    Deng, Zhihong
    Mao, Xuechun
    Peng, Yiyuan
    Yu, Chuyi
    [J]. TETRAHEDRON, 2016, 72 (09) : 1238 - 1243