Synthesis of Natural Product-like Polyheterocycles via One-Pot Cascade Oximation, C-H Activation, and Alkyne Annulation

被引：40
作者：
Zheng, Liyao [1 ]
Bin, Yunhui [1 ]
Wang, Yunpeng [1 ]
Hua, Ruimao [1 ]
机构：
[1] Tsinghua Univ, Dept Chem, Minist Educ, Key Lab Organ Optoelect & Mol Engn, Beijing 100084, Peoples R China
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2016年 / 81卷 / 19期
基金：
中国国家自然科学基金;
关键词：
CATALYZED INTRAMOLECULAR ANNULATION; DIVERSITY-ORIENTED SYNTHESIS; HETERO-DIELS-ALDER; CASSIA-SIAMEA; BOND ACTIVATION; DRUG DISCOVERY; PRIVILEGED STRUCTURES; RHODIUM CATALYSIS; ANTITUMOR AGENTS; CHEMICAL SPACE;
D O I：
10.1021/acs.joc.6b01460
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
An efficient protocol for the direct transformation of chrornan-4-ones to tricyclic fused pyridines with the skeleton of cassiarins, a family of alkaloids with antimalarial activity, was developed. Also, a general strategy for modular construction of polyheterocydes with diverse natural product-like skeletons was developed by using ketone-alkyne bifunctional substrates. These reactions involved a one-pot cascade oximation of ketones, rhodium-catalyzed C-H activation, and intermolecular/intramolecular alkyne annulations under mild conditions with high atom, step, and redox economy.
引用
收藏
页码：8911 / 8919
页数：9
相关论文
共 41 条
  • [31] Palladium-catalyzed double C-H activation: one-pot synthesis of benzo[c] pyrazolo[1,2-a]-cinnolin-1-ones from 5-pyrazolones and aryl iodides
    Fan, Zhoulong
    Wu, Kui
    Xing, Li
    Yao, Qizheng
    Zhang, Ao
    [J]. CHEMICAL COMMUNICATIONS, 2014, 50 (14) : 1682 - 1684
  • [32] Synthesis of 3-Methyleneisoindolin-1-ones via Rhodium(III)-Catalyzed C-H/N-H Activation and Annulation of N-Methoxybenzamides with Potassium Vinyltrifluoroborate
    Kumar, Vikash
    Gandeepan, Parthasarathy
    [J]. CHEMISTRY-AN ASIAN JOURNAL, 2024, 19 (22)
  • [33] Synthesis of Polysubstituted Furan Frameworks via [3+2] Annulation of N-Enoxyimides with Chelated Alkynes Initiated by Rh(III)-Catalyzed C-H Activation
    Wu, Min
    Wang, Yi
    Zhou, Jing
    Wang, Ting
    Gao, Hui
    Zhou, Zhi
    Yi, Wei
    [J]. ORGANIC LETTERS, 2023,
  • [34] Synthesis of Polysubstituted Furan Frameworks via [3+2] Annulation of N-Enoxyimides with Chelated Alkynes Initiated by Rh(III)-Catalyzed C-H Activation
    Wu, Min
    Wang, Yi
    Zhou, Jing
    Wang, Ting
    Gao, Hui
    Zhou, Zhi
    Yi, Wei
    [J]. ORGANIC LETTERS, 2023, 25 (14) : 2394 - 2399
  • [35] Rhodium-Catalyzed Spiro Indenyl Benzoxazine Synthesis via C-H Activation/Annulation of 3-Aryl-2H-Benzo[b][1,4]oxazines and Alkynes
    Tan, Heng
    Laishram, Ronibala Devi
    Zhang, Xuexin
    Shi, Guangrui
    Li, Kangkui
    Chen, Jingchao
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2020, 2020 (29) : 4542 - 4546
  • [36] Ru(II)-Catalyzed and Ligand-Controlled C-H Activation and Annulation via 1,2-Phenyl Shift: Synthesis of Quaternary Carbon-Centered Pyrimidoindolones
    Baruah, Swagata
    Saikia, Pallabi
    Duarah, Gauri
    Gogoi, Sanjib
    [J]. ORGANIC LETTERS, 2018, 20 (13) : 3753 - 3757
  • [37] Iodine-mediated sp3 C-H functionalization of methyl ketones: a one-pot synthesis of functionalized indolizines via the 1,3-dipolar cycloaddition reaction between pyridinium ylides and ynones
    Yavari, Issa
    Sheykhahmadi, Jamil
    Naeimabadi, Maryam
    Halvagar, Mohammad Reza
    [J]. MOLECULAR DIVERSITY, 2017, 21 (01) : 1 - 8
  • [38] Rh(iii)-catalyzed synthesis of tetracyclic isoquinolinium salts via C-H activation and [4+2] annulation of 1-phenyl-3,4-dihydroisoquinolines and alkynes in ethanol
    Dang, Xinxin
    He, Yu
    Liu, Yingtian
    Chen, Xuehong
    Li, Jun-Long
    Zhou, Xian-Li
    Jiang, Hezhong
    Li, Jiahong
    [J]. RSC ADVANCES, 2018, 8 (52): : 30050 - 30054
  • [39] Rhodium(III)-Catalyzed Synthesis of CF3-1H-benzo[de][1,8]naphthyridines via C-H Activation/Annulation of Benzimidates and CF3-Imidoyl Sulfoxonium Ylides
    Wen Si
    Ding Yuhao
    Tian Qingyu
    Ge Jin
    Cheng Guolin
    [J]. CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2024, 44 (01) : 291 - 300
  • [40] A Cascade Rh(III)-catalyzed C-H Activation/Chemodivergent Annulation of N-carbamoylindoles with Sulfoxonium Ylides for the Synthesis of Dihydropyrimidoindolone and Tricyclic [1,3]Oxazino[3,4-a]indol-1-ones Derivatives
    Xie, Hui
    Zhong, Mei
    Kang, Hua-Jie
    Shu, Bing
    Zhang, Shang-Shi
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2021, 363 (05) : 1436 - 1442
12345