Synthesis of Highly Fused Pyrano[2,3-b]pyridines via Rh(III)- Catalyzed C-H Activation and Intramolecular Cascade Annulation under Room Temperature

被引:23
作者
Han, Xu [1 ,2 ,3 ]
Gao, Feng [1 ,2 ]
Li, Chunpu [1 ,2 ,3 ]
Fang, Daqing [1 ,2 ,4 ]
Xie, Xiong [1 ,2 ,3 ]
Zhou, Yu [1 ,2 ,3 ]
Liu, Hong [1 ,2 ,3 ]
机构
[1] Chinese Acad Sci, State Key Lab Drug Res, Shanghai 201203, Peoples R China
[2] Chinese Acad Sci, CAS Key Lab Receptor Res, Shanghai Inst Mat Med, Shanghai 201203, Peoples R China
[3] Univ Chinese Acad Sci, Beijing 100049, Peoples R China
[4] Shenyang Pharmaceut Univ, Key Lab Struct Based Drug Design & Discovery, Minist Educ, Shenyang 110016, Peoples R China
基金
中国国家自然科学基金;
关键词
BOND ACTIVATION; FUNCTIONALIZATION; 1,2,4-TRIAZINES; CONSTRUCTION; HETEROCYCLES; NITROGEN; ACCESS;
D O I
10.1021/acs.joc.9b03102
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A facile access to the polycyclic-fused pyrano[2,3-b]pyridines has been established under room temperature via Rh(III)-catalyzed C-H bond activation and intramolecular cascade annulation. This strategy features high efficiency, unique versatility, and generality and it can occur under mild conditions in good to excellent yields. More importantly, this strategy can be extended to the late-stage functionalization of drugs possessing the CN group.
引用
收藏
页码:6281 / 6294
页数:14
相关论文
共 51 条
[41]   C-H bond activation enables the rapid construction and late-stage diversification of functional molecules [J].
Wencel-Delord, Joanna ;
Glorius, Frank .
NATURE CHEMISTRY, 2013, 5 (05) :369-375
[42]   Rhodium-Catalyzed Relay Carbenoid Functionalization of Aromatic C-H Bonds toward Fused Heteroarenes [J].
Wu, Xiaopeng ;
Xiong, Hao ;
Sun, Song ;
Cheng, Jiang .
ORGANIC LETTERS, 2018, 20 (05) :1396-1399
[43]   Propargyl Alcohols as One-Carbon Synthons: Redox-Neutral Rhodium(III)-Catalyzed C-H Bond Activation for the Synthesis of Isoindolinones Bearing a Quaternary Carbon [J].
Wu, Xiaowei ;
Wang, Bao ;
Zhou, Yu ;
Liu, Hong .
ORGANIC LETTERS, 2017, 19 (06) :1294-1297
[44]   Transition-Metal-Catalyzed Cross-Couplings through Carbene Migratory Insertion [J].
Xia, Ying ;
Qiu, Di ;
Wang, Jianbo .
CHEMICAL REVIEWS, 2017, 117 (23) :13810-13889
[45]   Rhodium-catalyzed C-H activation/annulation of amidines with 4-diazoisochroman-3-imines toward isochromeno[3,4-c]isoquinolines [J].
Xu, Shengbo ;
Qiao, Shanshan ;
Sun, Song ;
Yu, Jin-Tao ;
Cheng, Jiang .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2019, 17 (36) :8417-8424
[46]  
Yadav VK, 2005, EUR J ORG CHEM, V2005, P452
[47]   Discovery of N-[(4R)-6-(4-Chlorophenyl)-7-(2,4-dichlorophenyl)-2,2-dimethyl-3,4-dihydro-2H-pyrano[2,3-b]pyridin-4-yl]-5-methyl-1H-pyrazole-3-carboxamide (MK-5596) as a Novel Cannabinoid-1 Receptor (CB1R) Inverse Agonist for the Treatment of Obesity [J].
Yan, Lin ;
Huo, Pei ;
Debenham, John S. ;
Madsen-Duggan, Christina B. ;
Lao, Julie ;
Chen, Richard Z. ;
Xiao, Jing Chen ;
Shen, Chun-Pyn ;
Stribling, D. Sloan ;
Shearman, Lauren P. ;
Strack, Alison M. ;
Tsou, Nancy ;
Ball, Richard G. ;
Wang, Junying ;
Tong, Xinchun ;
Bateman, Thomas J. ;
Reddy, Vijay B. G. ;
Fong, Tung M. ;
Hale, Jeffrey J. .
JOURNAL OF MEDICINAL CHEMISTRY, 2010, 53 (10) :4028-4037
[48]   Manganese-Catalyzed ortho-C-H Alkenylation of Aromatic N-H Imidates with Alkynes: Versatile Access to Mono-Alkenylated Aromatic Nitriles [J].
Yang, Xiaoxu ;
Jin, Xiqing ;
Wang, Congyang .
ADVANCED SYNTHESIS & CATALYSIS, 2016, 358 (15) :2436-2442
[49]   Synthesis of Biaryl Compounds Using Tandem Ruthenium-Catalyzed Ring-Closing Metathesis [J].
Yoshida, Kazuhiro ;
Shida, Hiroaki ;
Takahashi, Hidetoshi ;
Yanagisawa, Akira .
CHEMISTRY-A EUROPEAN JOURNAL, 2011, 17 (01) :344-349
[50]   Direct Synthesis of 3-Acylindoles through Rhodium(III)-Catalyzed Annulation of N-Phenylamidines with α-Cl Ketones [J].
Zhou, Jianhui ;
Li, Jian ;
Li, Yazhou ;
Wu, Chenglin ;
He, Guoxue ;
Yang, Qiaolan ;
Zhou, Yu ;
Liu, Hong .
ORGANIC LETTERS, 2018, 20 (23) :7645-7649