Incorporating morpholine and oxetane into benzimidazolequinone anti-tumor agents : the discovery of 1,4,6,9-tetramethoxyphenazine from hydrogen peroxide and hydroiodic acid-mediated oxidative cyclizations

Conboy, Darren, Mirallai, Styliana I., Craig, Austin, McArdle, Patrick, Al-Kinani, Ali A., Barton, Stephen and Aldabbagh, Fawaz (2019) Incorporating morpholine and oxetane into benzimidazolequinone anti-tumor agents : the discovery of 1,4,6,9-tetramethoxyphenazine from hydrogen peroxide and hydroiodic acid-mediated oxidative cyclizations. The Journal of Organic Chemistry, 84(15), pp. 9811-9818. ISSN (print) 0022-3263

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Abstract

The reactivity of hydrogen peroxide and catalytic hydroiodic acid towards 3,6-dimethoxy-2-(cycloamino)anilines is tunable to give ring-fused benzimidazoles or 1,4,6,9-tetramethoxyphenazine in high yield. Mechanisms via a detected nitroso-intermediate are proposed for oxidative cyclization and the unexpected intermolecular displacement of the oxazine. An aqueous solution of molecular iodine is capable of the same transformations. Oxidative demethylation gave targeted benzimidazolequinones, including without cleavage of the incorporated oxetane.

Item Type: Article
Research Area: Chemistry
Faculty, School or Research Centre: Faculty of Science, Engineering and Computing
Faculty of Science, Engineering and Computing > School of Life Sciences, Pharmacy and Chemistry
Depositing User: Fawaz Al-Dabbagh
Date Deposited: 23 Jul 2019 07:58
Last Modified: 16 Sep 2019 08:07
DOI: https://doi.org/10.1021/acs.joc.9b01427
URI: http://eprints.kingston.ac.uk/id/eprint/43693

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