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钌(II)/聚乙二醇-400均相可循环催化体系中通过C-H/N-N键活化实现N-对甲苯磺酰腙导向环化反应:异喹啉的绿色合成

N-Tosylhydrazone directed annulation via C-H/N-N bond activation in Ru(ii)/PEG-400 as homogeneous recyclable catalytic system: a green synthesis of isoquinolines.

作者信息

Deshmukh Dewal S, Bhanage Bhalchandra M

机构信息

Department of Chemistry, Institute of Chemical Technology, Mumbai, India.

出版信息

Org Biomol Chem. 2018 Jul 4;16(26):4864-4873. doi: 10.1039/c8ob01082j.

DOI:10.1039/c8ob01082j
PMID:29926879
Abstract

A green and sustainable methodology for the synthesis of isoquinolines using Ru(ii)/PEG-400 as a homogeneous recyclable catalytic system has been demonstrated. N-Tosylhydrazone, a rarely explored directing group, has been successfully employed for an annulation type of reaction with alkynes via C-H/N-N activation. A short reaction time with a simple extraction procedure, a wide substrate scope with high yields of products, easily prepared substrates, biodegradable solvent, and scalability up to the gram level enhance the efficiency and sustainability of the proposed protocol. Further, the expensive ruthenium-based homogeneous catalytic system could be reused up to a fourth consecutive cycle without any loss in its activity.

摘要

已证明一种使用Ru(ii)/PEG - 400作为均相可循环催化体系合成异喹啉的绿色可持续方法。N-对甲苯磺酰腙,一种很少被研究的导向基团,已成功用于通过C-H/N-N活化与炔烃进行环化反应。反应时间短、萃取过程简单、底物范围广、产物收率高、底物易于制备、溶剂可生物降解以及可扩展至克级规模,提高了所提出方案的效率和可持续性。此外,昂贵的钌基均相催化体系可连续重复使用多达四个循环,而其活性没有任何损失。

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