Issue 8, 2019

Cooperative iridium complex-catalyzed synthesis of quinoxalines, benzimidazoles and quinazolines in water

Abstract

Herein, an efficient methodology for the synthesis of a diverse class of N-heterocyclic moieties, such as quinoxalines, benzimidazoles and quinazolines, was developed in water using bio-renewable alcohols. The quinoxalines were successfully synthesized from a wide range of diamines and nitroamines with diols in air. Interestingly, benzimidazoles and quinazolines were synthesized with excellent isolated yields without using any external base. Finally, the preparative scale synthesis of various N-heterocycles and pharmaceutically active quinoxalines established the practicability of this protocol. For this iridium system, a metal–ligand cooperative mechanism was proposed based on kinetic and DFT studies.

Graphical abstract: Cooperative iridium complex-catalyzed synthesis of quinoxalines, benzimidazoles and quinazolines in water

Supplementary files

Article information

Article type
Paper
Submitted
30 Nov 2018
Accepted
04 Mar 2019
First published
05 Mar 2019

Green Chem., 2019,21, 1999-2004

Cooperative iridium complex-catalyzed synthesis of quinoxalines, benzimidazoles and quinazolines in water

K. Chakrabarti, M. Maji and S. Kundu, Green Chem., 2019, 21, 1999 DOI: 10.1039/C8GC03744B

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