Copper-Catalyzed Synthesis of β- and δ-Carbolines by Double N-Arylation of Primary Amines

被引：7

作者：

Ban Van Phuc ^{[1
]}

Ha Nam Do ^{[2
]}

Nguyen Minh Quan ^{[3
]}

Nguyen Ngoc Tuan ^{[1
]}

Nguyen Quang An ^{[1
]}

Nguyen Van Tuyen ^{[1
,3
]}

Hoang Le Tuan Anh ^{[4
]}

Tran Quang Hung ^{[1
,3
]}

Tuan Thanh Dang ^{[2
]}

Langer, Peter ^{[5
,6
]}

机构：

[1] Vietnam Acad Sci & Technol, Inst Chem, 18-Hoang Quoc Viet, Hanoi, Vietnam

[2] Vietnam Natl Univ VNU, Hanoi Univ Sci, Fac Chem, 19 Le Thanh Tong, Hanoi, Vietnam

[3] Vietnam Acad Sci & Technol, Grad Univ Sci & Technol, 18 Hoang Quoc Viet, Hanoi, Vietnam

[4] Vietnam Acad Sci & Technol, Ctr Res & Technol Transfer, 18 Hoang Quoc Viet, Hanoi, Vietnam

[5] Univ Rostock, Inst Chem, Albert Einstein Str 3a, D-18059 Rostock, Germany

[6] Univ Rostock eV, Leibniz Inst Katalyse, Albert Einstein Str 3a, D-18059 Rostock, Germany

来源：

SYNLETT | 2021年 / 32卷 / 10期

关键词：

catalysis; heterocycles; cross-coupling; cyclizations; copper; BIOLOGICAL EVALUATION; GAMMA-CARBOLINES; HOST MATERIALS; IN-VITRO; DERIVATIVES; CYCLIZATION; ANALOGS; ALPHA; CRYPTOLEPINE; ALKALOIDS;

D O I：

10.1055/s-0040-1720461

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Two efficient and practical approaches are reported for the synthesis of beta- and delta-carbolines from 3,4-dibromopyridine. The synthesis is based on site-selective Cu-catalyzed double C-N coupling reactions and subsequent annulations by twofold Pd-catalyzed C-N coupling with amines.

引用

页码：1004 / 1008

页数：5

共 50 条

[21] Copper-Catalyzed Sequential N-Arylation and Aerobic Oxidation: Synthesis of Quinazoline Derivatives
Liu, Qing
Zhao, Yufen
Fu, Hua
Cheng, Changmei
SYNLETT, 2013, 24 (16) : 2089 - 2094
[22] Base-assisted, copper-catalyzed N-arylation of (benz)imidazoles and amines with diarylborinic acids
Guan, Changwei
Feng, Yuanyuan
Zou, Gang
Tang, Jie
TETRAHEDRON, 2017, 73 (49) : 6906 - 6913
[23] Copper-catalyzed N-arylation of amines/amides in poly(ethylene glycol) as recyclable solvent medium
Chandrasekhar, S
Sultana, SS
Yaragorla, SR
Reddy, NR
SYNTHESIS-STUTTGART, 2006, (05): : 839 - 842
[24] Aqueous copper-catalyzed N-arylation of indoles: the surfactant strategy
Liu, Songbai
Zhou, Jiahui
NEW JOURNAL OF CHEMISTRY, 2013, 37 (08) : 2537 - 2540
[25] An Effective N-Ligand for Copper-Catalyzed N-Arylation of Triazole
Yang, Yan
Jin, Yong-Sheng
Hu, Hong-Gang
Zhao, Qing-Jie
Zou, Yan
Wu, Qui-Ye
ASIAN JOURNAL OF CHEMISTRY, 2010, 22 (09) : 7435 - 7437
[26] Benzotriazole: an efficient ligand for the copper-catalyzed N-arylation of indoles
Verma, Akhilesh Kumar
Singh, Jaspal
Larock, Richard C.
TETRAHEDRON, 2009, 65 (40) : 8434 - 8439
[27] Copper-catalyzed N-arylation of heterocycles in ethylene glycol medium
Sharifi, A. (sharifi@ccerci.ac.ir), 1600, Sharif University of Technology (23):
[28] Copper-Catalyzed Selective N-Arylation of Oxadiazolones by Diaryliodonium Salts
Soldatova, Natalia S.
Semenov, Artem V.
Geyl, Kirill K.
Baykov, Sergey V.
Shetnev, Anton A.
Konstantinova, Anna S.
Korsakov, Mikhail M.
Yusubov, Mekhman S.
Postnikov, Pavel S.
ADVANCED SYNTHESIS & CATALYSIS, 2021, 363 (14) : 3566 - 3576
[29] Mild copper-catalyzed N-arylation of azaheterocycles with aryl halides
Kuil, M
Bekedam, EK
Visser, GM
van den Hoogenband, A
Terpstra, JW
Kamer, PCJ
van Leeuwen, PWNM
van Strijdonck, GPF
TETRAHEDRON LETTERS, 2005, 46 (14) : 2405 - 2409
[30] Copper-catalyzed denitrogenative N-arylation of sulfoximines and sulfonamides with arylhydrazines
Dong, Wanrong
Liu, Chaoyang
Ma, Xinchi
Zhang, Yingjun
Peng, Zhihong
Xie, Dexun
An, Delie
TETRAHEDRON, 2019, 75 (29) : 3886 - 3893

← 1 2 3 4 5 →