3-Aroylindoles via Copper-Catalyzed Cyclization of N-(2-Iodoaryl)enaminones

被引：23

作者：

Bernini, Roberta ^{[2
,3
]}

Cacchi, Sandro ^{[1
]}

Fabrizi, Giancarlo ^{[1
]}

Filisti, Eleonora ^{[1
]}

Sferrazza, Alessio ^{[2
,3
]}

机构：

[1] Univ Roma La Sapienza, Dipartimento Chim & Tecnol Farmaco, I-00185 Rome, Italy

[2] Univ Tuscia, Dipartimento ABAC, I-01100 Viterbo, Italy

[3] Consorzio Univ La Chim Ambiente, I-01100 Viterbo, Italy

来源：

SYNLETT | 2009年 / 09期

关键词：

indoles; enaminones; cyclization; copper; catalysis; ACTIVATING-FACTOR ANTAGONISTS; 2,3-DISUBSTITUTED INDOLES; BOND FORMATION; PALLADIUM; ARYLATION; ACYLATION; 3-ACYLINDOLES; ENAMINONES; ELLIPTICINE; PYRROLES;

D O I：

10.1055/s-0029-1216742

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

3-Aroylindoles have been prepared via copper-catalyzed cyclization of N-(2-iodoaryl)enaminones, readily available from 2-iodoanilines and alpha,beta-ynones. The reaction tolerates a variety of useful functionalities including ether, keto, cyano, bromo, and chloro substituents. This indole synthesis can also be carried out from 2-iodoanilines and alpha,beta-ynones through a sequential process that omits the isolation of enaminone intermediates.

引用

页码：1480 / 1484

页数：5

共 50 条

[21] Synthesis of 3-Aryl-2-(trifluoromethyl)indoles via Copper-Catalyzed Hydroarylation and Subsequent Cadogan Cyclization
Yamamoto, Yoshishiko
Ohkubo, Erina
Shibuya, Masatoshi
ADVANCED SYNTHESIS & CATALYSIS, 2017, 359 (10) : 1747 - 1751
[22] Biomimetic synthesis of (-)-chaetominine epimers via copper-catalyzed radical cyclization
Deng, Xu
Liang, Kangjiang
Tong, Xiaogang
Ding, Ming
Li, Dashan
Xia, Chengfeng
TETRAHEDRON, 2015, 71 (22) : 3699 - 3704
[23] An Alternative Approach to Synthesize Sildenafil via Improved Copper-Catalyzed Cyclization
Odilov, Abdullajon
Gong, Xudong
Qin, Hongjian
Bonku, Emmanuel Mintah
Zhu, Fuqiang
Yang, Feipu
Shen, Jingshan
JOURNAL OF ORGANIC CHEMISTRY, 2024, 89 (10): : 7303 - 7311
[24] Regioselective access to polycyclic N-heterocycles via homogeneous copper-catalyzed cascade cyclization of allenynes
Kua-Fei Wei
Qing Liu
Guang Ma
Xiao-Lei Jiang
Xiu-Hong Zhu
Guang-Xin Ru
Wen-Bo Shen
Communications Chemistry, 6
[25] Copper-Catalyzed Oxidative [1+2+1+2] Cascade Cyclization of N,N-Dimethyl Enaminones with Benzylamines: A Facile Access to Functionalized 1,4-Dihydropyridines
Sun, Yulin
Chai, Zhangmengjie
Liu, Donghan
Zhang, Mingshuai
Chen, Longkun
Liu, Zhuoyuan
Wang, Yongchao
Yu, Fuchao
CHEMISTRY-A EUROPEAN JOURNAL, 2023, 29 (28)
[26] Facile synthesis of isoquinolines and isoquinoline N-oxides via a copper-catalyzed intramolecular cyclization in water
Zhang, Lujun
Xiong, Wenfang
Yao, Biao
Liu, Haitao
Li, Meng
Qin, Yu
Yu, Yujian
Li, Xu
Chen, Meng
Wu, Wanqing
Li, Jianxiao
Wang, Jinliang
Jiang, Huanfeng
RSC ADVANCES, 2022, 12 (47) : 30248 - 30252
[27] Regioselective access to polycyclic N-heterocycles via homogeneous copper-catalyzed cascade cyclization of allenynes
Wei, Kua-Fei
Liu, Qing
Ma, Guang
Jiang, Xiao-Lei
Zhu, Xiu-Hong
Ru, Guang-Xin
Shen, Wen-Bo
COMMUNICATIONS CHEMISTRY, 2023, 6 (01)
[28] Copper-catalyzed N-(hetero)arylation of amino acids in water
Sharma, Krishna K.
Mandloi, Meenakshi
Rai, Neha
Jain, Rahul
RSC ADVANCES, 2016, 6 (99) : 96762 - 96767
[29] Synthesis of Phthalans Via Copper-Catalyzed Enantioselective Cyclization/Carboetherification of 2-Vinylbenzyl Alcohols
Chen, Dake
Chemler, Sherry R.
ORGANIC LETTERS, 2018, 20 (20) : 6453 - 6456
[30] Synthesis of phthalans via copper-catalyzed enantioselective cyclization/carboetherification of 2-vinylbenzyl alcohols
Chen, Dake
Chemler, Sherry
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2019, 257

← 1 2 3 4 5 →