Michael additions of o-nitrophenylacetonitrile have been investigated. The adducts are formed diastereoselectively under mild conditions. Higher temperatures result in an unusual annulation involving intramolecular nucleophilic attack of an enolate on the nitro group, giving rise to 2,3,4-trisubstituted quinolines. In contrast, under similar conditions ethyl o-nitrophenylacetic acid reacts with N-methylmaleimide to give an N-hydroxyindole. A possible explanation for the divergent chemistry, and mechanisms for these reactions are proposed.
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