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Issue 8, 2017
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An alternative method to access diverse N,N′-diquaternised-3,3′-biquinoxalinium “biquinoxen” dications

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Abstract

An alternative synthetic route for the design of N,N′-diquaternised-3,3′-biquinoxalinium “biquinoxen” dications is reported, involving oxidative radical coupling of dithionite reduced quinoxaline quaternary salts. Although the reaction is not regioselective, leading to relatively modest yields (up to 32%), the advantages of this new synthetic protocol lie in a simple potentially gram scale synthesis using inexpensive easily accessible reagents with no metal catalysts and no purification steps. Thus whereas the method reported previously to access the N,N′-dimethyl-3,3′-biquinoxalinium, “methylbiquinoxen” precursor gave higher yield than the new method reported here, this new method avoids the limitation of using scarce oxonium reagents. Overall, the new protocol is a robust synthetic strategy which offers new design possibilities.

Graphical abstract: An alternative method to access diverse N,N′-diquaternised-3,3′-biquinoxalinium “biquinoxen” dications

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Publication details

The article was received on 13 Feb 2017, accepted on 01 Mar 2017 and first published on 02 Mar 2017


Article type: Paper
DOI: 10.1039/C7NJ00531H
Citation: New J. Chem., 2017,41, 2949-2954
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    An alternative method to access diverse N,N′-diquaternised-3,3′-biquinoxalinium “biquinoxen” dications

    N. Leblanc, S. Sproules and A. K. Powell, New J. Chem., 2017, 41, 2949
    DOI: 10.1039/C7NJ00531H

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