Abstract
The reactivity of hydrogen peroxide and catalytic hydroiodic acid toward 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.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Acids / chemistry
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Antineoplastic Agents / chemical synthesis
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Antineoplastic Agents / chemistry*
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Benzimidazoles / chemical synthesis
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Benzimidazoles / chemistry*
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Catalysis
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Cyclization
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Drug Discovery*
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Ethers, Cyclic / chemistry*
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Hydrogen Peroxide / chemistry
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Iodine Compounds / chemistry
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Molecular Structure
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Morpholines / chemistry*
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Oxidation-Reduction
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Phenazines / chemical synthesis
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Phenazines / chemistry*
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Quinones / chemical synthesis
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Quinones / chemistry*
Substances
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Acids
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Antineoplastic Agents
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Benzimidazoles
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Ethers, Cyclic
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Iodine Compounds
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Morpholines
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Phenazines
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Quinones
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hydroiodic acid
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morpholine
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Hydrogen Peroxide
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oxetane