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
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共 41 条
[21]   One-pot synthesis of fluorescent 2,4-dialkenylindoles by rhodium-catalyzed dual C-H functionalization [J].
Chen, Hui ;
Lin, Cong ;
Xiong, Chunhua ;
Liu, Zhanxiang ;
Zhang, Yuhong .
ORGANIC CHEMISTRY FRONTIERS, 2017, 4 (03) :455-459
[22]   One-Pot Protocol To Synthesize 2-Aminophenols from Anilines via Palladium-Catalyzed C-H Acetoxylation [J].
Zhao, Junhao ;
Huang, Yifeng ;
Ma, Guojian ;
Lin, Ling ;
Feng, Pengju .
ORGANOMETALLICS, 2019, 38 (09) :2084-2091
[23]   Synthesis of Highly Fused Pyrano[2,3-b]pyridines via Rh(III)- Catalyzed C-H Activation and Intramolecular Cascade Annulation under Room Temperature [J].
Han, Xu ;
Gao, Feng ;
Li, Chunpu ;
Fang, Daqing ;
Xie, Xiong ;
Zhou, Yu ;
Liu, Hong .
JOURNAL OF ORGANIC CHEMISTRY, 2020, 85 (10) :6281-6294
[24]   Pd-Catalyzed C-H/N-H Arylation: One-Pot Synthesis of Indolo[1,2-f]phenanthridines [J].
Kong, Lingkai ;
Yao, Qiyi ;
Wang, Mengdan ;
Sun, Ruizhuo ;
Li, Yanzhong .
CHEMISTRYSELECT, 2018, 3 (02) :456-460
[25]   Synthesis of isochromenones and oxepines via Pd-catalyzed cascade cyclization of alkynes and benzynes involving C-H activation [J].
Parthasarathy, Kanniyappan ;
Han, Han ;
Prakash, Chandran ;
Cheng, Chien-Hong .
CHEMICAL COMMUNICATIONS, 2012, 48 (52) :6580-6582
[26]   One-Pot Synthesis of Highly Fluorescent Pyrido[1,2-a]indole Derivatives through C-H/N-H Activation: Photophysical Investigations and Application in Cell Imaging [J].
Samala, Srinivas ;
Pallavi, Pragyan ;
Kumar, Ravi ;
Arigela, Rajesh K. ;
Singh, Gajendra ;
Ampapathi, Ravi Sankar ;
Priya, Amulya ;
Datta, Sunando ;
Patra, Abhijit ;
Kundu, Bijoy .
CHEMISTRY-A EUROPEAN JOURNAL, 2014, 20 (44) :14344-14350
[27]   Synthesis of Indazolo[2,1-a]Cinnolines via Rhodium (III)-Catalyzed C-H activation/annulation under mild conditions [J].
Hou, Wei ;
Xiong, Huan ;
Bai, Ruisong ;
Xiao, Zaozao ;
Su, Lin ;
Ruan, Bengfang Helen ;
Xu, Hongtao .
TETRAHEDRON, 2019, 75 (30) :4005-4009
[28]   Palladium(II)-Catalyzed Sequential C-H Arylation/Aerobic Oxidative C-H Amination: One-Pot Synthesis of Benzimidazole-Fused Phenanthridines from 2-Arylbenzimidazoles and Aryl Halides [J].
Zhao, Gongyuan ;
Chen, Chunxia ;
Yue, Yixia ;
Yu, Yanhan ;
Peng, Jinsong .
JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (05) :2827-2834
[29]   Construction of Natural-Product-Like Cyclophane-Braced Peptide Macrocycles via sp3 C-H Arylation [J].
Li, Bo ;
Li, Xinghua ;
Han, Boyang ;
Chen, Zhijie ;
Zhang, Xuekai ;
He, Gang ;
Chen, Gong .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2019, 141 (23) :9401-9407
[30]   Synthesis of CF3-Containing Spiro-[Indene-Proline] Derivatives via Rh(III)-Catalyzed C-H Activation/Annulation [J].
Bubnova, Alexandra S. ;
Vorobyeva, Daria V. ;
Godovikov, Ivan A. ;
Smol'yakov, Alexander F. ;
Osipov, Sergey N. .
MOLECULES, 2023, 28 (23)
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