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

Leblanc, N., Sproules, S. and Powell, A. K. (2017) An alternative method to access diverse N,N′-diquaternised-3,3′-biquinoxalinium “biquinoxen” dications. New Journal of Chemistry, 41(8), pp. 2949-2954. (doi: 10.1039/C7NJ00531H)

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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.

Item Type:Articles
Glasgow Author(s) Enlighten ID:Sproules, Dr Stephen
Authors: Leblanc, N., Sproules, S., and Powell, A. K.
College/School:College of Science and Engineering > School of Chemistry
Journal Name:New Journal of Chemistry
Publisher:Royal Society of Chemistry
ISSN (Online):1369-9261
Published Online:02 March 2017
Copyright Holders:Copyright © 2017 The Royal Society of Chemistry and the Centre National de la Recherche Scientifique
First Published:First published in New Journal of Chemistry 41(8): 2949-2954
Publisher Policy:Reproduced in accordance with the publisher copyright policy

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