Iodine-Catalyzed Synthesis of Benzo-β-carbolines through Desulfurative Cyclization of 2-(1H-Indol-3-ylsulfanyl)-phenylamines with Aryl Methyl Ketones

被引：9

作者：

Marupalli, Sasi Sree ^{[1
]}

Arockiaraj, Mariyaraj ^{[1
]}

Singh, Gargi ^{[1
]}

Rajeshkumar, Venkatachalam ^{[1
]}

机构：

[1] Natl Inst Technol Warangal, Dept Chem, Organ Synth & Catalysis Lab, Hanumakonda 506004, Telangana, India

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2023年 / 88卷 / 17期

关键词：

BETA-CARBOLINE DERIVATIVES; SEQUENTIAL ADDITION; ALKALOIDS; ISOTHIOCYANATES; ANTIMALARIAL; SCAFFOLD; INDOLES; ACCESS;

D O I：

10.1021/acs.joc.3c00657

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A noveltransition metal-free strategy for the synthesis of benzene-fused & beta;-carboline scaffolds has been developed. This protocol offersa rapid and direct pathway to access the benzene fused & beta;-carbolinefrom 2-(1H-indol-3-ylsulfanyl)-phenylamines and arylmethyl ketones using an efficient catalytic system of I-2/DMSO. The present mild protocol proceeds through the sequentialreactions of Kornblum oxidation, Pictet-Spengler cyclization,and desulfurization to afford the desired products in excellent yieldsup to 99%. Moreover, this method has a wide range of substrate toleranceand is operationally simple and applicable in gram-scale synthesis.

引用

页码：12783 / 12791

页数：9

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