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)

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.

• Item Type: Articles
• Status: Published
• Refereed: Yes
• 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: 1144-0546
• 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