Efficient synthesis of aryl-substituted carbazoles via tandem double or triple suzuki coupling and cadogan cyclization

被引：5

作者：

Kim, Hyeong Seok ^{[1
]}

Goo, Deuk-Young ^{[1
]}

Woo, Sang Kook ^{[1
]}

机构：

[1] Univ Ulsan, Dept Chem, 93 Daehak Ro,Nam Gu, Ulsan 44610, South Korea

来源：

TETRAHEDRON | 2017年 / 73卷 / 11期

关键词：

Aryl-substituted carbazole; Tandem reaction; Cadgan cyclization; Suzuki coupling; One-pot reaction; FUNCTIONALIZED CARBAZOLES; TRIETHYL PHOSPHITE; ORGANIC-SYNTHESIS; NITRO-COMPOUNDS; BORONIC ACID; DERIVATIVES; INHIBITORS; REDUCTION; ALKALOIDS; PHOSPHORUS;

D O I：

10.1016/j.tet.2017.01.038

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient one-step method to prepare aryl-substituted carbazoles via tandem double or triple C-C bond formations by multiple Suzuki couplings and C-N bond formation by Cadogan cyclization has been developed. The developed method employs commercially available or easily preparable poly-bromonitrobenzenes and arylboronic acids as starting materials, tolerates various functional groups, and provides good yields. (C) 2017 Elsevier Ltd. All rights reserved.

引用

页码：1413 / 1423

页数：11

共 50 条

[1] Synthesis of aryl-substituted indanones and indenes via a highly efficient ligand-free palladium-catalyzed Suzuki coupling process
Song, Yuming
Xie, Yamei
Chen, Minjian
Qu, Jingping
Hu, Hongfan
Lang, Xiaomei
Xue, Shan
Ran, Yin
Xin, Shixuan
[J]. ARKIVOC, 2016, : 306 - 327
[2] An Efficient Synthesis of Aryl-Substituted Pyrroles by the Suzuki-Miyaura Coupling Reaction of SEM-Protected Pyrroles
Cui, Keli
Gao, Meng
Zhao, Hongyi
Zhang, Dongfeng
Yan, Hong
Huang, Haihong
[J]. MOLECULES, 2019, 24 (08)
[3] Facile synthesis of aryl-substituted pyridines via Suzuki-Miyaura approach
Karadeniz, Eda
Zora, Metin
Kilicaslan, Nihan Zulay
[J]. TETRAHEDRON, 2015, 71 (47) : 8943 - 8952
[4] Synthesis of aryl-substituted quinolines and tetrahydroquinolines through Suzuki-Miyaura coupling reactions
Okten, Salih
[J]. JOURNAL OF CHEMICAL RESEARCH, 2019, 43 (7-8) : 274 - 280
[5] An effective synthesis of β-aryl substituted isotetronic acids via Suzuki coupling
Huan Sheng Chen Xia Ping Ma Zhi Ming Li Quan Rui Wang Feng Gang Tao Department of Chemistry
[J]. Chinese Chemical Letters, 2008, (11) : 1309 - 1311
[6] An effective synthesis of β-aryl substituted isotetronic acids via Suzuki coupling
Chen, Huan Sheng
Ma, Xia Ping
Li, Zhi Ming
Wang, Quan Rui
Tao, Feng Gang
[J]. CHINESE CHEMICAL LETTERS, 2008, 19 (11) : 1309 - 1311
[7] Efficient synthesis of substituted piperazinones via tandem reductive amination-cyclization
Dinsmore, CJ
Zartman, CB
[J]. TETRAHEDRON LETTERS, 2000, 41 (33) : 6309 - 6312
[8] Facile Synthesis of Aryl-Substituted Cycloarenes via Bismuth(III) Triflate-Catalyzed Cyclization of Vinyl Ethers
Fan, Wei
Han, Yi
Dong, Shaoqiang
Li, Guangwu
Lu, Xuefeng
Wu, Jishan
[J]. CCS CHEMISTRY, 2021, 3 (05): : 1445 - 1452
[9] SYNTHESIS OF ARYL-SUBSTITUTED ALLYLIC AMINES VIA PALLADIUM-CATALYZED COUPLING OF ARYL IODIDES, NONCONJUGATED DIENES, AND AMINES
LAROCK, RC
WANG, Y
LU, YD
RUSSELL, CE
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (26): : 8107 - 8114
[10] Efficient synthesis of substituted terphenyls by suzuki coupling reaction
Chaumeil, H
Le Drian, C
Defoin, A
[J]. SYNTHESIS-STUTTGART, 2002, (06): : 757 - 760

← 1 2 3 4 5 →