Three-Component One-Pot Synthesis of Highly Functionalized Bis-Indole Derivatives

被引:16
作者
Chen, Xue-Bing [1 ]
Xiong, Sheng-Li [1 ]
Xie, Zhi-Xu [1 ]
Wang, Yong-Chao [2 ]
Liu, Wei [1 ]
机构
[1] Honghe Univ, Sch Sci, Mengzi 661100, Yunnan, Peoples R China
[2] Yunnan Normal Univ, Sch Vocat & Tech Educ, Kunming 650092, Yunnan, Peoples R China
来源
ACS OMEGA | 2019年 / 4卷 / 07期
关键词
MULTIPLE C-C; FACILE SYNTHESIS; EFFICIENT CONSTRUCTION; SELECTIVE INHIBITORS; CONVERGENT SYNTHESIS; DOMINO REACTIONS; CASCADE REACTION; MULTICOMPONENT; ALKALOIDS; ENAMINONES;
D O I
10.1021/acsomega.9b01159
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
In this study, we detail the development of a concise and efficient three-component protocol for the regioselective synthesis of highly functionalized bis-indoles through a one-pot, two-step sequential process starting from enaminones 1, indoles 2, and acenaphthylene-1,2-dione 3 that is catalyzed by piperidine and p-methyl benzenesulfonic acid. This protocol has several advantages including simplicity of experimental operation, high efficiency of bond formation, ready availability and low cost of starting materials, environmentally benign conditions, and target molecular diversity.
引用
收藏
页码:11832 / 11837
页数:6
相关论文
共 51 条
[1]   Indirubin and indigo are potent aryl hydrocarbon receptor ligands present in human urine [J].
Adachi, J ;
Mori, Y ;
Matsui, S ;
Takigami, H ;
Fujino, J ;
Kitagawa, H ;
Miller, CA ;
Kato, T ;
Saeki, K ;
Matsuda, T .
JOURNAL OF BIOLOGICAL CHEMISTRY, 2001, 276 (34) :31475-31478
[2]   Ammonia-Doped Polyaniline-Graphitic Carbon Nitride Nanocomposite as a Heterogeneous Green Catalyst for Synthesis of Indole-Substituted 4H-Chromenes [J].
Bahuguna, Ashish ;
Choudhary, Priyanka ;
Chhabra, Tripti ;
Krishnan, Venkata .
ACS OMEGA, 2018, 3 (09) :12163-12178
[3]   Construction of Fully Substituted 2-Pyridone Derivatives via Four-Component Branched Domino Reaction Utilizing Microwave Irradiation [J].
Bai, Hairui ;
Sun, Rongrong ;
Liu, Shitao ;
Yang, Lijuan ;
Chen, Xuebing ;
Huang, Chao .
JOURNAL OF ORGANIC CHEMISTRY, 2018, 83 (20) :12535-12548
[4]   Bisindole alkaloids of the topsentin and hamacanthin classes from a marine sponge Spongosorites sp. [J].
Bao, Baoquan ;
Sun, Qishi ;
Yao, Xinsheng ;
Hong, Jongki ;
Lee, Chong-O. ;
Cho, Hee Young ;
Jung, Jee H. .
JOURNAL OF NATURAL PRODUCTS, 2007, 70 (01) :2-8
[5]   TOPSENTINS, NEW TOXIC BIS-INDOLE ALKALOIDS FROM THE MARINE SPONGE TOPSENTIA-GENITRIX [J].
BARTIK, K ;
BRAEKMAN, JC ;
DALOZE, D ;
STOLLER, C ;
HUYSECOM, J ;
VANDEVYVER, G ;
OTTINGER, R .
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1987, 65 (09) :2118-2121
[6]   An Environmentally Benign Catalytic Method for Versatile Synthesis of 1,4-Dihydropyridines via Multicomponent Reactions [J].
Cao, Shuo ;
Zhong, Shanshan ;
Hu, Changfeng ;
Wan, Jie-Ping ;
Wen, Chengping .
CHINESE JOURNAL OF CHEMISTRY, 2015, 33 (05) :568-572
[7]   Indole-to-Carbazole Strategy for the Synthesis of Substituted Carbazoles under Metal-Free Conditions [J].
Chen, Shanping ;
Li, Yuxia ;
Ni, Penghui ;
Huang, Huawen ;
Deng, Guo-Jun .
ORGANIC LETTERS, 2016, 18 (20) :5384-5387
[8]   Efficient construction of C-N and C-S bonds in 2-iminothiazoles via cascade reaction of enaminones with potassium thiocyanate [J].
Chen, Xue-Bing ;
Wang, Xue-Quan ;
Song, Jia-Na ;
Yang, Qing-Li ;
Huang, Chao ;
Liu, Wei .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2017, 15 (17) :3611-3615
[9]   Site-Selective Convergent Synthesis of Spiroacridines through a Cascade Reaction of Enaminones with Acenaphthoquinone: An Efficient Construction of Multiple C-C and C-Heteroatom Bonds [J].
Chen, Xue-Bing ;
Wang, Xue-Quan ;
Hong, Yong ;
Liu, Wei .
ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2016, 5 (07) :907-913
[10]   Highly Diastereoselective Convergent Synthesis of Polycyclic Pyrroles with Consecutive Quaternary Stereocenters: Cascade Construction of Multiple C-C and C-Hetero Bonds [J].
Chen, Xue-Bing ;
Liu, Zhi-Cheng ;
Lin, Xin-Rong ;
Huang, Rong ;
Yan, Sheng-Jiao ;
Lin, Jun .
ACS SUSTAINABLE CHEMISTRY & ENGINEERING, 2014, 2 (10) :2391-2398