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Vincent Fagan, Sarah Bonham, Patrick McArdle, Michael P. Carty and Fawaz Aldabbagh Synthesis and Toxicity of New Ring-Fused Imidazo[5,4-f]benzimidazolequinones and Mechanism Using Amine N-Oxide Cyclizations European Journal of Organic Chemistry 2012

Version of Record online: 13 FEB 2012 | DOI: 10.1002/ejoc.201101687

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Double oxidative cyclisations of o-tert-aminoacetanilides give [1,4-oxazino]- and alicyclic ring-fused imidazo[5,4-f]benzimidazoles. The hydrogen-bonded orientation of the amine N-oxide intermediate is used to propose a mechanism. Unsymmetrical quinone derivatives are more potent than previously reported imidazobenzimidazolequinones.

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