Studies on Tertiary Amine Oxides. XXIV. Reactions of Aromatic N-Oxides with Enamines of Cyclohexanone in the Presence of Acylating Agents (1)
Year: 1965
Type: article
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.
DOI: 10.1248/cpb.13.912
Authors: Masatomo Hamana, Hiroshi Noda
Language: English
Subfield: Organic Chemistry
Field: Chemistry
Domain: Physical Sciences
Open Access status: bronze
OpenAlex ID: W1982993263