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
[31]   Substrate Activation Strategies in Rhodium(III)-Catalyzed Selective Functionalization of Arenes [J].
Song, Guoyong ;
Li, Xingwei .
ACCOUNTS OF CHEMICAL RESEARCH, 2015, 48 (04) :1007-1020
[32]   C-C, C-O and C-N bond formation via rhodium(III)-catalyzed oxidative C-H activation [J].
Song, Guoyong ;
Wang, Fen ;
Li, Xingwei .
CHEMICAL SOCIETY REVIEWS, 2012, 41 (09) :3651-3678
[33]   FURTHER INTRAMOLECULAR REACTIONS OF 1,2,4-TRIAZINES - SYNTHESIS OF FURO[2,3-B]PYRIDINES AND DIHYDROPYRANO[2,3-B]PYRIDINES [J].
TAYLOR, EC ;
MACOR, JE .
TETRAHEDRON LETTERS, 1986, 27 (04) :431-432
[34]   INTRAMOLECULAR DIELS-ALDER REACTIONS OF 1,2,4-TRIAZINES - A GENERAL-SYNTHESIS OF FURO[2,3-B]PYRIDINES, 2,3-DIHYDROPYRANO[2,3-B]PYRIDINES, AND PYRROLO[2,3-B]PYRIDINES [J].
TAYLOR, EC ;
MACOR, JE ;
PONT, JL .
TETRAHEDRON, 1987, 43 (21) :5145-5158
[35]   A mild alkaline hydrolysis of N- and N,N-substituted amides and nitriles [J].
Theodorou, Vassiliki ;
Paraskevopoulos, Georgios ;
Skobridis, Konstantinos .
ARKIVOC, 2015, :101-112
[36]   A Fast Way to Fluorescence: A Fourfold Domino Reaction to Condensed Polycyclic Compounds [J].
Tietze, Lutz F. ;
Eichhorst, Christoph ;
Hungerland, Tim ;
Steinert, Markus .
CHEMISTRY-A EUROPEAN JOURNAL, 2014, 20 (39) :12553-12558
[37]   Rh(III)-Catalyzed C-C/C-N Coupling of Imidates with α-Diazo Imidamide: Synthesis of Isoquinoline-Fused Indoles [J].
Wang, He ;
Li, Lei ;
Yu, Songjie ;
Li, Yunyun ;
Li, Xingwei .
ORGANIC LETTERS, 2016, 18 (12) :2914-2917
[38]   Synthesis of 1H-Indazoles from Imidates and Nitrosobenzenes via Synergistic Rhodium/Copper Catalysis [J].
Wang, Qiang ;
Li, Xingwei .
ORGANIC LETTERS, 2016, 18 (09) :2102-2105
[39]   Rh(III)-Catalyzed C-H Bond Activation for the Construction of Heterocycles with sp3-Carbon Centers [J].
Wang, Run ;
Xie, Xiong ;
Liu, Hong ;
Zhou, Yu .
CATALYSTS, 2019, 9 (10)
[40]   Ligand-enabled meta-C-H activation using a transient mediator [J].
Wang, Xiao-Chen ;
Gong, Wei ;
Fang, Li-Zhen ;
Zhu, Ru-Yi ;
Li, Suhua ;
Engle, Keary M. ;
Yu, Jin-Quan .
NATURE, 2015, 519 (7543) :334-338