Marupalli Sasi Sree, Arockiaraj Mariyaraj, Singh Gargi, Rajeshkumar Venkatachalam
Organic Synthesis & Catalysis Lab, Department of Chemistry, National Institute of Technology Warangal, Hanumakonda 506004, Telangana, India.
J Org Chem. 2023 Sep 1;88(17):12783-12791. doi: 10.1021/acs.joc.3c00657. Epub 2023 Aug 16.
A novel transition metal-free strategy for the synthesis of benzene-fused β-carboline scaffolds has been developed. This protocol offers a rapid and direct pathway to access the benzene fused β-carboline from 2-(1-indol-3-ylsulfanyl)-phenylamines and aryl methyl ketones using an efficient catalytic system of I/DMSO. The present mild protocol proceeds through the sequential reactions of Kornblum oxidation, Pictet-Spengler cyclization, and desulfurization to afford the desired products in excellent yields up to 99%. Moreover, this method has a wide range of substrate tolerance and is operationally simple and applicable in gram-scale synthesis.
一种用于合成苯并稠合β-咔啉支架的新型无过渡金属策略已被开发出来。该方案提供了一条快速直接的途径，使用I/DMSO高效催化体系，从2-(1-吲哚-3-基硫烷基)-苯胺和芳基甲基酮制备苯并稠合β-咔啉。目前这种温和的方案通过Kornblum氧化、Pictet-Spengler环化和脱硫的顺序反应，以高达99%的优异产率得到所需产物。此外，该方法具有广泛的底物耐受性，操作简单，适用于克级规模的合成。
