Rh(III)-catalyzed C-H activation/intramolecular annulation for the synthesis of N-methoxydihydropyrimidin-2-one fused heterocycles

被引:1
|
作者
Huang, Youchun [1 ]
Kang, Ke [1 ]
Zhong, Xiuwen [1 ]
Yu, Yongping [1 ]
Chen, Wenteng [1 ]
机构
[1] Zhejiang Univ, Coll Pharmaceut Sci, Hangzhou 310058, Zhejiang, Peoples R China
关键词
C -H activation; Intramolecular annulation; Rh(III)-catalyzed; N-Methoxydihydropyrimidin-2-one; CHEMODIVERGENT ANNULATIONS; REVERSE-TRANSCRIPTASE; SULFOXONIUM YLIDES; INHIBITION; ACTIVATION; INDOLES;
D O I
10.1016/j.tetlet.2022.154311
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A facile rhodium-catalyzed C-H activation/intramolecular annulation strategy for N-methoxydihydropyrimidin-2-one was well realized in water media. Moreover, this Rh(III)-catalytic system facilitated the construction of N-methoxydihydropyrimidin-2-one scaffolds reminiscent of unnatural amino alcohols, transformation to pyran-2-one fused heterocycles as well as late-stage modification of drug molecules. Also, the protocol was easily scaled up to a gram-scale level. And H2O was proposed to act as an alternative coordination molecule to accelerate the generation of active Rh(III) catalyst species. (c) 2022 Elsevier Ltd. All rights reserved.
引用
收藏
页数:6
相关论文
共 50 条
  • [21] Synthesis of Furanone-Fused 1,2-Benzothiazine by Rh(III)-Catalyzed C-H Activation: Regioselective Oxidative Annulation Leading to in Situ Lactonization in One Pot
    Hanchate, Vinayak
    Kumar, Anil
    Prabhu, Kandikere Ramaiah
    JOURNAL OF ORGANIC CHEMISTRY, 2019, 84 (17): : 11335 - 11342
  • [22] Synthesis of fused aromatic heterocycles by palladium-catalyzed C-H activation chemistry
    Pacheco, Jarren
    Knoerzer, Timm
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2018, 255
  • [23] Synthesis of indene-fused spiro-dibenz(ox)azepines via Rh(iii)-catalyzed cascade regioselective C-H activation/annulation
    Naskar, Koushik
    Karmakar, Sudip
    Mondal, Imtiaj
    Sarkar, Writhabrata
    Roy, Shantonu
    Roy, Anupam
    Deb, Indubhusan
    CHEMICAL COMMUNICATIONS, 2023, 59 (50) : 7751 - 7754
  • [24] Dual C-H activation: Rh(iii)-catalyzed cascade π-extended annulation of 2-arylindole with benzoquinone
    Zhang, Qijing
    Li, Qianrong
    Wang, Chengming
    RSC ADVANCES, 2021, 11 (21) : 13030 - 13033
  • [25] Rh(III)-Catalyzed C-H Functionalization/Annulation of 1-Arylindazolones: Divergent Synthesis of Fused Indazolones and Allyl Indazolones
    Shu, Bing
    Song, Jia-Lin
    Chen, Shao-Yong
    Zheng, Yi-Chuan
    Zhang, Shang-Shi
    JOURNAL OF ORGANIC CHEMISTRY, 2023, 88 (06): : 3499 - 3508
  • [26] One-Pot Rh(III)-Catalyzed Twofold C-H Activation/Oxidative Annulation of N-Arylpyrroles with Alkynes to Fluorescent Ullazines
    Otero-Riesgo, Sergio
    Varela, Jesus A.
    Saa, Carlos
    ADVANCED SYNTHESIS & CATALYSIS, 2024, 366 (10) : 2312 - 2323
  • [27] Rh(III)-Catalyzed [3+2] Annulation and C-H Alkenylation of Indoles with 1,3-Diynes by C-H Activation
    Kumar, Sanjeev
    Nunewar, Saiprasad
    Usama, Khan Mohammad
    Kanchupalli, Vinaykumar
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2021, 2021 (15) : 2223 - 2229
  • [28] Three-Component Synthesis of Isoquinolone Derivatives via Rh(III)-Catalyzed C-H Activation and Tandem Annulation
    Yang, Zhenke
    Liu, Jidan
    Li, Yuting
    Ding, Jiawen
    Zheng, Liyao
    Liu, Zhao-Qing
    JOURNAL OF ORGANIC CHEMISTRY, 2022, 87 (21): : 14809 - 14818
  • [29] N-Doped Cationic PAHs by Rh(III)-Catalyzed Double C-H Activation and Annulation of 2-Arylbenzimidazoles with Alkynes
    Villar, Jose M.
    Suarez, Jaime
    Varela, Jesus A.
    Saa, Carlos
    ORGANIC LETTERS, 2017, 19 (07) : 1702 - 1705
  • [30] Recent advances in the synthesis of nitrogen heterocycles via Rh(<sc>iii</sc>)-catalyzed chelation-assisted C-H activation/annulation with diazo compounds
    Liu, Jidan
    Liang, Ruilian
    Yan, Qinglian
    Zheng, Liyao
    Liu, Zhao-Qing
    Pu, Shouzhi
    ORGANIC CHEMISTRY FRONTIERS, 2025,