Hydride Transfer Involved Redox-Neutral Cascade Cyclizations for Construction of Spirocyclic Bisoxindoles Featuring a [3,4]-Fused Oxindole Moiety

被引：81

作者：

Li, Shuai-Shuai ^{[1
]}

Zhu, Shuai ^{[1
]}

Chen, Chunqi ^{[1
]}

Duan, Kang ^{[1
]}

Liu, Qing ^{[3
]}

Xiao, Jian ^{[1
,2
]}

机构：

[1] Qingdao Agr Univ, Coll Chem & Pharmaceut Sci, Qingdao 266109, Peoples R China

[2] Qingdao Agr Univ, Coll Marine Sci & Engn, Qingdao 266109, Peoples R China

[3] Shandong Univ Sci & Technol, Coll Chem & Environm Engn, Qingdao 266590, Peoples R China

来源：

ORGANIC LETTERS | 2019年 / 21卷 / 04期

关键词：

ONE-POT SYNTHESIS; C(SP(3))-H BOND FUNCTIONALIZATION; NAPHTHO-FUSED OXINDOLES; EFFICIENT SYNTHESIS; TRANSFER/CYCLIZATION; ACTIVATION; TETRAHYDROQUINOLINES; CONSTITUENTS; ANNULATIONS; DERIVATIVES;

D O I：

10.1021/acs.orglett.8b04100

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The hydride transfer involved redox-neutral cascade cyclization has been developed to construct the spirocyclic bisoxindoles featuring a [3,4]-fused oxindole moiety from rationally designed C4-amine-substituted isatins, affording the diverse tricyclic [3,4]-fused oxindoles with three consecutive chiral centers in good yields and excellent diastereoselectivities (>20:1).

引用

页码：1058 / 1062

页数：5

共 77 条

[1] Antitumor activity of substituted E-3-(3,4,5-trimethoxybenzylidene)-1,3-dihydroindol-2-ones [J].

Andreani, Aldo ;

Burnelli, Silvia ;

Granaiola, Massimiliano ;

Leoni, Alberto ;

Locatelli, Alessandra ;

Morigi, Rita ;

Rambaldi, Mirella ;

Varoli, Lucilla ;

Kunkel, Mark W. .

JOURNAL OF MEDICINAL CHEMISTRY, 2006, 49 (23) :6922-6924

[2]

[Anonymous], 2017, BIG DAT RESP DIG AGR, DOI [10.1145/1143518.1143522, DOI 10.1145/1143518.1143522]

[3] DDQ-mediated Direct Intramolecular-Dehydrogenative-Coupling (IDC): Expeditious Approach to the Tetracyclic Core of Ergot Alkaloids [J].

Bhunia, Subhajit ;

Ghosh, Santanu ;

Dey, Dhananjay ;

Bisai, Alakesh .

ORGANIC LETTERS, 2013, 15 (10) :2426-2429

[4] Pd-Catalyzed Dehydrogenative Aryl-Aryl Bond Formation via Double C(sp2)-H Bond Activation:, Efficient Synthesis of [3,4]-Fused Oxindoles [J].

Bunescu, Ala ;

Piou, Tiffany ;

Wang, Qian ;

Zhu, Jieping .

ORGANIC LETTERS, 2015, 17 (02) :334-337

[5] Development of Synthetic Methodologies via Catalytic Enantioselective Synthesis of 3,3-Disubstituted Oxindoles [J].

Cao, Zhong-Yan ;

Zhou, Feng ;

Zhou, Jian .

ACCOUNTS OF CHEMICAL RESEARCH, 2018, 51 (06) :1443-1454

[6] Construction of Oxadiazepines via Lewis Acid-Catalyzed Tandem 1,5-Hydride Shift/Cyclization [J].

Chang, Yong-Zhi ;

Li, Ming-Lei ;

Zhao, Wen-Feng ;

Wen, Xiaoan ;

Sun, Hongbin ;

Xu, Qing-Long .

JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (19) :9620-9627

[7] Metal-Free Oxidation/C(sp3)-H Functionalization of Unactivated Alkynes Using Pyridine-N-Oxide as the External Oxidant [J].

Chen, Dian-Feng ;

Han, Zhi-Yong ;

He, Yu-Ping ;

Yu, Jie ;

Gong, Liu-Zhu .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (49) :12307-12310

[8] Catalytic functionalization of tertiary alcohols to fully substituted carbon centres [J].

Chen, Long ;

Yin, Xiao-Ping ;

Wang, Cui-Hong ;

Zhou, Jian .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2014, 12 (32) :6033-6048

[9] Organocatalytic Synthesis of Spiro[pyrrolidin-3,3′-oxindoles] with High Enantiopurity and Structural Diversity [J].

Chen, Xiao-Hua ;

Wei, Qiang ;

Luo, Shi-Wei ;

Xiao, Han ;

Gong, Liu-Zhu .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (38) :13819-13825

[10] Organocatalytic Asymmetric Assembly Reactions: Synthesis of Spirooxindoles via Organocascade Strategies [J].

Cheng, Daojuan ;

Ishihara, Yoshihiro ;

Tan, Bin ;

Barbas, Carlos F., III .

ACS CATALYSIS, 2014, 4 (03) :743-762

← 1 2 3 4 5 6 7 8 →