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Communication | Regular issue | Vol 3, No. 1, 1975, pp.19-23
Published online, 1st January, 1970
DOI: 10.3987/R-1975-01-0019
Reactions of Aromatic N-Oxides with O-Benzoyl Aromatic Aldehyde Cyanohydrins in Acetic Anhydride

Toshiyasu Endo, Seitaro Saeki, and Masatomo Hamana*

*Faculty of Pharmaceutical Sciences, Kyushu University, 3-1-1 Maidashi, Higashi-ku, Fukuoka 812-8582, Japan

Abstract

Quinoline N-oxide (I) readily reacts in hot acetic anhydride with some O-benzoyl aromatic aldehyde cyanohydrins (Va-d) to produce O-benzoylcyanohydrins (VIa-d) of 2-quinolyl aryl ketones which are easily convertible to the corresponding ketones (VIIa-d) by alkaline hydrolysis. Similar reactions occur also with N-oxides of isoquinoline, pyridine and phenanthridine (II, III and IV). The derivatives of benzaldehyde and p-chloro- benzaldehyde resist the reaction.