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

被引：63

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

来源：

ORGANIC LETTERS | 2019年 / 21卷 / 16期

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

页码：6225 / 6230

页数：6

共 22 条

[1] Hexafluoroisopropanol-Mediated Redox-Neutral α-C(sp3)-H Functionalization of Cyclic Amines via Hydride Transfer
Shen, Yao-Bin
Wang, Lin-Xuan
Sun, Yun-Ming
Dong, Feng-Ying
Yu, Liping
Liu, Qing
Xiao, Jian
JOURNAL OF ORGANIC CHEMISTRY, 2020, 85 (04): : 1915 - 1926
[2] Redox-Neutral Cascade Dearomatization of Indoles via Hydride Transfer: Divergent Synthesis of Tetrahydroquinoline-Fused Spiroindolenines
Shen, Yao-Bin
Li, Long-Fei
Xiao, Ming-Yan
Yang, Jian-Ming
Liu, Qing
Xiao, Jian
JOURNAL OF ORGANIC CHEMISTRY, 2019, 84 (21): : 13935 - 13947
[3] Water mediated redox-neutral cleavage of arylalkenes via photoredox catalysis
Liao, Ke
Fang, Yuqi
Sheng, Lei
Chen, Jiean
Huang, Yong
NATURE COMMUNICATIONS, 2024, 15 (01)
[4] Rapid assembly of cyclopentene spiroisoindolinones via a rhodium-catalysed redox-neutral cascade reaction
Yuan, Tingting
Pi, Chao
You, Chang
Cui, Xiuling
Du, Sidong
Wan, Ting
Wu, Yangjie
CHEMICAL COMMUNICATIONS, 2019, 55 (02) : 163 - 166
[5] A concise method for cyclic gem-difluoroacyl scaffolds via visible-light-mediated redox-neutral cascade radical cyclization of alkenes
Liu, Zhen
Wei, Yin
Shi, Min
CATALYSIS SCIENCE & TECHNOLOGY, 2022, 12 (17) : 5325 - 5331
[6] Cyclopropanation of N-vinylimides via a redox-neutral photocatalysed radical addition/anionic cyclisation process
Huai, Linge
Zhang, Li
Wang, Zhentao
Wu, Hao
Fang, Yewen
ORGANIC CHEMISTRY FRONTIERS, 2023, 10 (05) : 1245 - 1251
[7] Acylperoxycoumarins as ortho-CH Acylating Agent via a Palladium(II)-Catalyzed Redox-Neutral Process
Mohanta, Prakash Ranjan
Banerjee, Arghya
Santra, Sourav Kumar
Behera, Ahalya
Patel, Bhisma K.
ADVANCED SYNTHESIS & CATALYSIS, 2016, 358 (13) : 2047 - 2052
[8] Controllable construction of pharmaceutically significant scaffolds of 2,3-dihydroquinolin-4-one and benzoazepine-5-one via redox-neutral cascade hydride transfer/cyclization
Xie, Ronghao
Chen, Shixiao
Wang, Yufeng
Yin, Xiangcong
Li, Shuai-Shuai
Xu, Lubin
Wang, Liang
ORGANIC CHEMISTRY FRONTIERS, 2022, 9 (19) : 5205 - 5212
[9] Deracemisation of Mandelic Acid to Optically Pure Non-Natural L-Phenylglycine via a Redox-Neutral Biocatalytic Cascade
Resch, Verena
Fabian, Walter M. F.
Kroutil, Wolfgang
ADVANCED SYNTHESIS & CATALYSIS, 2010, 352 (06) : 993 - 997
[10] Diastereoselective Spirocyclization of Cyclic N-Sulfonyl Ketimines with Nitroalkenes via Iridium-Catalyzed Redox-Neutral Cascade Reaction
Mishra, Aniket
Mukherjee, Upasana
Sarkar, Writhabrata
Meduri, Sudha Lahari
Bhowmik, Arup
Deb, Indubhusan
ORGANIC LETTERS, 2019, 21 (07) : 2056 - 2059

← 1 2 3 →