Studies on tertiary amine oxides. XXIV. Reactions of aromatic N-oxides with enamines of cyclohexanone in the presence of acylating agents. (1).

Abstract

Quinoline 1-oxide racted smoothly with cyclohexanone enamines in the presence of acylating agent, producing 2-(2-quinolyl) cyclohexanone as a major product in a good yield after treatment of the raction mixture with hydrochloric acid. The effectiveness of acylating agents was as follows : benzoyl chloride>tosyl chloride>acetic anhydride∼acetyl chloride. The sequence of the reactivity of enamines was morpholine>piperidine->pyrrolidine-enamine. The reaction of pyridine 1-oxide and isoquinoline 2-oxide similarly proceeded in good yields, 2-(2-pyridyl)- and 2-(1-isoquinoly)-cyclohexanone being obtained, respectively. The structural elucidation of the products was effected by chemical methods and the examinations of their infrared and ultraviolet spectra.