Syntheses of heterocyclic compounds. Part XXV. Action of acid on NN-disubstituted o-nitroanilines: benzimidazole N-oxide formation and nitro-group rearrangements
- 1 January 1973
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- p. 696-701
- https://doi.org/10.1039/p19730000696
Abstract
A variety of NN-disubstituted o-nitroanilines are shown to give benzimidazole N-oxides, often in high yield, when heated in mineral acid solution. The product is accompanied by small amounts of the denitrated parent compound and p-nitro- and 2,4-dinitro-derivatives. Irradiation of acidic solutions of NN-disubstituted o-nitroanilines similarly yields either the corresponding benzimidazole N-oxide or the benzimidazole by different mechanisms and with no concomitant rearrangement of nitro-groups. Synthetic and mechanistic implications are discussed.Keywords
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