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

被引:30
|
作者
Jiang, Xin [1 ,2 ]
Yang, Qin [1 ,2 ]
Yuan, Jianjun [1 ,2 ]
Deng, Zhihong [1 ,2 ]
Mao, Xuechun [1 ,2 ]
Peng, Yiyuan [1 ,2 ]
Yu, Chuyi [3 ]
机构
[1] Minist Educ, Jiangxi Provinces Key Lab Green Chem, Key Lab Funct Small Organ Mol, Nanchang 330022, Peoples R China
[2] Jiangxi Normal Univ, Nanchang 330022, Peoples R China
[3] Chinese Acad Sci, Inst Chem, CAS Key Lab Mol Recognit & Funct, Beijing 330022, Peoples R China
基金
中国国家自然科学基金;
关键词
Rhodium catalysis; C-H activation; Aza-Michael addition; Quinazolin-4-one; Pyrrolo[2,1-b]quinazolin-9(1H)-one; Tandem reaction; DIELS-ALDER REACTION; BOND FORMATION; QUINAZOLINE; QUINOLINE;
D O I
10.1016/j.tet.2016.01.020
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
In this paper, a rhodium-catalyzed reaction of 2-arylquinazolin-4-ones with acrylates is described, leading to pyrrolo[2, 1-b]quinazolin-9(1H)-one derivatives with high efficiency and good tolerance of functional groups. In the reactions, it is believed that tandem C-H activation and aza-Michael addition are involved. (C) 2016 Elsevier Ltd. All rights reserved.
引用
收藏
页码:1238 / 1243
页数:6
相关论文
共 50 条
  • [1] Rhodium-catalyzed C-H bond activation alkylation and cyclization of 2-arylquinazolin-4-ones
    Lou, Minhao
    Deng, Zhihong
    Mao, Xuechun
    Fu, Yang
    Yang, Qin
    Peng, Yiyuan
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2018, 16 (11) : 1851 - 1859
  • [2] Ruthenium-catalyzed oxidative coupling of 2-aryl-4-quinazolinones with olefins: synthesis of pyrrolo[2,1-b]quinazolin-9(1H)-one motifs
    Zheng, Yong
    Song, Wei-Bin
    Zhang, Shu-Wei
    Xuan, Li-Jiang
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2015, 13 (23) : 6474 - 6478
  • [3] SYNTHESIS OF TETRAHYDROPYRIDO-[2,1-B]QUINAZOLIN-10(1H)-ONE AND PENTAHYDROAZEPINO[2,1-B]QUINAZOLIN-11(1H)-ONE DERIVATIVES
    JAIN, MP
    GUPTA, VN
    ATAL, CK
    INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 1985, 24 (03): : 336 - 337
  • [4] Domino synthesis of fused pyrazolo[5,1-b]quinazolin-9(1H)-ones catalyzed by CuI via subsequent Michael addition and elimination
    Zhang, Yan
    Xu, Jing
    Li, Chao
    Wang, Xiang-Shan
    TETRAHEDRON, 2015, 71 (46) : 8732 - 8737
  • [5] Iodine-catalyzed synthesis of fused tetracyclic pyridazino[6,1-b] pyrrolo[1,2-a]quinazolin-9(1H)-one derivatives via a tandem reaction
    Zhang, Wen-Ting
    Qiang, Wen-Wen
    Yao, Chang-Sheng
    Wang, Xiang-Shan
    TETRAHEDRON, 2016, 72 (17) : 2178 - 2185
  • [6] Direct access to pyrido/pyrrolo[2,1-b]quinazolin-9(1H)-ones through silver-mediated intramolecular alkyne hydroamination reactions
    Wang, Hengshuai
    Jiao, Shengchao
    Chen, Kerong
    Zhang, Xu
    Zhao, Linxiang
    Liu, Dan
    Zhou, Yu
    Liu, Hong
    BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2015, 11 : 416 - 424
  • [7] NEW METHOD FOR THE PREPARATION OF 2-CARBOALKOXYPYRAZOLO[5,1-B]QUINAZOLIN-9(1H)ONES
    BEAM, CF
    BROWN, J
    DAWKINS, DR
    FIVES, WP
    HEINDEL, ND
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 1979, 16 (05) : 957 - 960
  • [8] Selenium-Catalyzed Oxidative C-H Amination of (E)-3-(Arylamino)-2-styrylquinazolin-4(3H)-ones: A Metal-Free Synthesis of 1,2-Diarylpyrazolo[5,1-b]quinazolin-9(1H)-ones
    Zhang, Yetong
    Shao, Yinlin
    Gong, Julin
    Zhu, Jianghe
    Cheng, Tianxing
    Chen, Jiuxi
    JOURNAL OF ORGANIC CHEMISTRY, 2019, 84 (05): : 2798 - 2807
  • [9] Metal-free sequential decarbonylative annulation of N-cyanamides for the construction of 2,3-dihydropyrrolo[2,1-b]quinazolin-9(1H)-ones
    Liu, Xueke
    Qian, Ping
    Wang, Yi
    Pan, Yi
    ORGANIC CHEMISTRY FRONTIERS, 2017, 4 (12): : 2370 - 2374
  • [10] One pot synthesis of pyrrolo[3,2,1-de]phenanthridines from 7-phenylindoles via tandem C-H olefination/aza-Michael addition
    Yuan, Yumeng
    Pan, Guoshuai
    Zhang, Xiaofeng
    Huang, Qiufeng
    ORGANIC CHEMISTRY FRONTIERS, 2020, 7 (01): : 53 - 63