Studies on Tertiary Amine Oxides. LXXX. Reaction of Quinoline 1-Oxide with Phenylacetic Anhydride
Search this Article
Treatment of quinoline 1-oxide (1) with phenylacetic acid and acetic anhydride in boiling benzene for 10 h gave benzaldehyde (2), quinoline (3), 2-benzylquinoline (4), 2-benzoylquinoline (5), phenyl-di (2-quinolyl) carbinol (6), di (2-quinolyl) ketone (7), and N-(2-quinolyl)-2-benzylidene-1,2-dihydroquinoline (8) in small yields. The reaction of 1 with phenylacetic anhydride in boiling benzene for 10 h afforded 1,3-diphenyl-1-(2-quinolyl) acetone (9) and dibenzyl ketone (10) together with small amounts of 2,3,and 5. Further, it was found that phenylacetic anhydride undergoes decarboxylative coupling upon heating with tertiary amines to give 10. The mechanisms of these reactions are discussed.
- Chemical & pharmaceutical bulletin
Chemical & pharmaceutical bulletin 32(10), 3886-3891, 1984-10-25
The Pharmaceutical Society of Japan