Controllable Syntheses of Spiroindolenines and Benzazepinoindoles via Hexafluoroisopropanol-Mediated Redox-Neutral Cascade Process

被引:71
作者
Bai, Guangxian [1 ]
Dong, Fengying [1 ]
Xu, Lubin [1 ]
Liu, Yongjun [2 ]
Wang, Liang [1 ]
Li, Shuai-Shuai [1 ]
机构
[1] Qingdao Agr Univ, Coll Chem & Pharmaceut Sci, Qingdao 266109, Shandong, Peoples R China
[2] Qingdao Univ Sci & Technol, Coll Chem & Mol Engn, Zhengzhou Rd 53, Qingdao 266042, Shandong, Peoples R China
关键词
C(SP(3))-H BOND FUNCTIONALIZATION; INTRAMOLECULAR HYDRIDE TRANSFER; C-H ACTIVATION; ENANTIOSELECTIVE SYNTHESIS; ALLYLIC DEAROMATIZATION; FLUORINATED ALCOHOLS; SPIROCYCLIC INDOLENINES; CYCLIC AMINALS; CONSTRUCTION; TRANSFER/CYCLIZATION;
D O I
10.1021/acs.orglett.9b02051
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The pharmaceutically intriguing spiroindolenines incorporating tetrahydroquinoline were constructed via a hexafluoroisopropanol-promoted redox-neutral cascade cyclization from readily available starting materials. The benzazepinoindole skeletons could also be facilely accessed via one-pot sequential operation. Distinctive features of these transformations include their controllable access of the two privileged skeletons, high efficiency, simple operation, and mild reaction conditions.
引用
收藏
页码:6225 / 6230
页数:6
相关论文
共 82 条
[31]   Redox-triggered cascade dearomative cyclizations enabled by hexafluoroisopropanol [J].
Li, Shuai-Shuai ;
Lv, Xintong ;
Ren, Didi ;
Shao, Chang-Lun ;
Liu, Qing ;
Xiao, Jian .
CHEMICAL SCIENCE, 2018, 9 (43) :8253-8259
[32]   Organocatalytic C(sp3)-H Functionalization via Carbocation-Initiated Cascade [1,5]-Hydride Transfer/Cyclization: Synthesis of Dihydrodibenzo[b,e]azepines [J].
Li, Shuai-Shuai ;
Zhou, Lan ;
Wang, Liang ;
Zhao, Huaili ;
Yu, Liping ;
Xiao, Jian .
ORGANIC LETTERS, 2018, 20 (01) :138-141
[33]   Enantioselective synthesis of benzazepinoindoles bearing trifluoromethylated quaternary stereocenters catalyzed by chiral spirocyclic phosphoric acids [J].
Li, Xuejian ;
Chen, Di ;
Gu, Haorui ;
Lin, Xufeng .
CHEMICAL COMMUNICATIONS, 2014, 50 (56) :7538-7541
[34]   Rhodium-Catalyzed Intramolecular Difluoromethylenative Dearomatization of Phenols [J].
Li, Yajun ;
Zhang, Lisi ;
Zhang, Li ;
Wu, Yongming ;
Gong, Yuefa .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2013, 2013 (35) :8039-8047
[35]   Dearomatizing Spiroannulation Reagents: Direct Access to Spirocycles from Indoles and Dihalides [J].
Liddon, John T. R. ;
Rossi-Ashton, James A. ;
Taylor, Richard J. K. ;
Unsworth, William P. .
ORGANIC LETTERS, 2018, 20 (11) :3349-3353
[36]   Catalyst-Driven Scaffold Diversity: Selective Synthesis of Spirocycles, Carbazoles and Quinolines from Indolyl Ynones [J].
Liddon, John T. R. ;
James, Michael J. ;
Clarke, Aimee K. ;
O'Brien, Peter ;
Taylor, Richard J. K. ;
Unsworth, William P. .
CHEMISTRY-A EUROPEAN JOURNAL, 2016, 22 (26) :8777-8780
[37]   Arboflorine, an unusual pentacyclic monoterpenoid indole alkaloid incorporating a third nitrogen atom [J].
Lim, KH ;
Kam, TS .
ORGANIC LETTERS, 2006, 8 (08) :1733-1735
[38]   Substrate-controlled divergent synthesis of polycyclic indoloazepines and indolodiazepines via 1,5-hydride shift/7-cyclization cascades [J].
Liu, Siyuan ;
Qu, Jingping ;
Wang, Baomin .
CHEMICAL COMMUNICATIONS, 2018, 54 (57) :7928-7931
[39]   Aromatization-Driven Cascade [1,5]-Hydride Transfer/Spirocyclization Promoted by Fluorinated Alcohols [J].
Lv, Xintong ;
Hu, Fangzhi ;
Duan, Kang ;
Li, Shuai-Shuai ;
Liu, Qing ;
Xiao, Jian .
JOURNAL OF ORGANIC CHEMISTRY, 2019, 84 (04) :1833-1844
[40]   Synthesis of Spiroindolenines via Regioselective Gold(I)-Catalyzed Cyclizations of N-Propargyl Tryptamines [J].
Magne, Valentin ;
Marinetti, Angela ;
Gandon, Vincent ;
Voituriez, Arnaud ;
Guinchard, Xavier .
ADVANCED SYNTHESIS & CATALYSIS, 2017, 359 (22) :4036-4042