Issue 26, 2018

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

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.

Graphical abstract: 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

Supplementary files

Article information

Article type
Paper
Submitted
09 May 2018
Accepted
08 Jun 2018
First published
08 Jun 2018

Org. Biomol. Chem., 2018,16, 4864-4873

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

D. S. Deshmukh and B. M. Bhanage, Org. Biomol. Chem., 2018, 16, 4864 DOI: 10.1039/C8OB01082J

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