A Tandem Approach to Functionalized Carbazoles from Indoles via Two Successive Regioselective Oxidative Heck Reactions Followed by Thermal Electrocyclization

被引：89

作者：

Laha, Joydey K. ^{[1
]}

Dayal, Neetu ^{[1
]}

机构：

[1] Natl Inst Pharmaceut Educ & Res, Dept Pharmaceut Technol Proc Chem, Sas Nagar 160062, Punjab, India

来源：

ORGANIC LETTERS | 2015年 / 17卷 / 19期

关键词：

AMINO-ALPHA-CARBOLINES; C-H FUNCTIONALIZATION; AROMATIC-SUBSTITUTION; C(SP(2))-H BONDS; CARBAZOMYCIN-G; ALKENYLATION; PALLADIUM(II); ALKALOIDS; AMINATION; ARYLATION;

D O I：

10.1021/acs.orglett.5b02265

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A direct one-pot approach to the synthesis of carbazoles (mono-, di-, and trisubstituted) and alpha-carbolines from readily available indoles or 7-azaindoles and alkenes is described. Based on mechanistic studies, the tandem reaction follows the sequence: palladium-catalyzed regioselective C-3 alkenylation/palladium-catalyzed C-2 alkenylation/thermal electrocyclization.

引用

页码：4742 / 4745

页数：4

共 5 条

[1] Tandem approach to carbazoles and alpha-carbolines from indoles and 7-azaindoles via successive Fujiwara-Moritani reactions followed by cyclization
Laha, Joydev
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2016, 251
[2] Pd(II) supramolecular cage-catalyzed successive oxidative coupling: One-pot and regioselective synthesis of functionalized carbazoles from indoles
Wu, Xi-Ren
Peng, He-Long
Wei, Lian-Qiang
Li, Li-Ping
Yao, Su-Yang
Ye, Bao-Hui
CATALYSIS COMMUNICATIONS, 2019, 124 : 12 - 18
[3] THERMAL 1,6-ELECTROCYCLIZATION REACTIONS OF ACCEPTOR-SUBSTITUTED 2,3-DIVINYL-1H-INDOLES YIELDING FUNCTIONALIZED CARBAZOLES
PINDUR, U
ADAM, R
HELVETICA CHIMICA ACTA, 1990, 73 (04) : 827 - 838
[4] Two-Step Continuous Synthesis of Dicarbonyl Indoles via I2/DMSO-Promoted Oxidative Coupling: A Green and Practical Approach to Valuable Diketones from Aryl Acetaldehydes
Guo, Shiyu
Hua, Jiawei
Dai, Zhongxue
Yang, Zhao
Fang, Zheng
Guo, Kai
ACS SUSTAINABLE CHEMISTRY & ENGINEERING, 2018, 6 (06): : 7979 - 7988
[5] Universal Two-Step Approach to Degradable and Electroactive Block Copolymers and Networks from Combined Ring-Opening Polymerization and Post-Functionalization via Oxidative Coupling Reactions
Guo, Baolin
Finne-Wistrand, Anna
Albertsson, Ann-Christine
MACROMOLECULES, 2011, 44 (13) : 5227 - 5236

← 1 →