Abstract
Reaction of aromatic N-oxide with enol ether in the presence of benzoyl chloride was examined. 2-Ethoxycyclohexene (II) reacted readily with quinoline 1-oxides (I, IV) and isoquinoline 2-oxide (VI), producing α-2-cyclohexanonyl derivatives (III, V, VII) in fairly good yields. Similarly, the reaction of I with 2-ethoxypropene (IX), methyl vinyl ether (XI) and dihydropyrane (XIV) gave 2-acetonyl-(X), 2-(2-methoxyvinyl)-(XII) and 2-(5-dihydropyranyl)-quinolines (XV), respectively. Nucleophilic reactivity of enol ether in this reaction was considerably lower compared with that of enamine ; no satisfactory result was obtained with II and pyridine 1-oxide and also with I and furan, thiophene and anisole under similar conditions.
