Bronsted Acid-Mediated Cycloaromatization of 1H-Indol-2-yl Propargyl Benzoates to 7H-Benzo[c] carbazoles

被引：8
|
作者：
Tan, Javey Khiapeng [1 ]
Mathiew, Mitch [1 ]
Nayak, Sanatan [1 ]
Chan, Philip Wai Hong [1 ,2 ]
机构：
[1] Monash Univ, Sch Chem, Clayton, Vic 3800, Australia
[2] Univ Warwick, Dept Chem, Coventry CV4 7AL, W Midlands, England
来源：
CHEMISTRY-AN ASIAN JOURNAL | 2017年 / 12卷 / 13期
基金：
澳大利亚研究理事会;
关键词：
alkynes; Bronsted acid; homogeneous catalysis; nitrogen heterocycles; silica gel; MEYER-SCHUSTER REARRANGEMENT; GOLD-CATALYZED CYCLOISOMERIZATION; SOLVENT-FREE CONDITIONS; DIELS-ALDER REACTION; SILICA-GEL; SUBSTITUTED CARBAZOLES; EFFICIENT SYNTHESIS; ESTERS; DERIVATIVES; CASCADE;
D O I：
10.1002/asia.201700419
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
A synthetic method for the efficient assembly of benzo[c] carbazole derivatives that relies on silica gel-activated benzoic acid-mediated cycloaromatization of 1H-indol-2-yl propargyl benzoates under atmospheric conditions is described. Robust with a variety of substitution patterns tolerated, the reaction provides a one-step strategy to construct a member of the N-heterocycles family in good to excellent yields. A tentative mechanism is proposed in which the cycloaromatization process is thought to involve a Bronsted acid-mediated formal 1,3-acyloxy migration/6p-electrocyclization pathway.
引用
收藏
页码：1475 / 1479
页数：5
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