95113-34-1Relevant academic research and scientific papers
Studies on Tertiary Amine Oxides. LXXX.1) Reaction of Quinoline 1-oxide with Phenylacetic Anhydride
Funakoshi, Kazuhisa,Mizuoka, Masae,Wada, Kazuko,Saeki, Seitaro,Hamana, Masatomo
, p. 3886 - 3891 (2007/10/02)
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 anhydrideundergoes decarboxylative coupling upon heating with tertiary amines to give 10.The mechamisms of these reactions are discussed. Keywords --- nucleophilic reaction; oxidative decarboxylation; decarboxylative coupling; benzaldehyde; 2-benzylquinoline; phenyl-di(2-quinolyl)carbinol; N-(2-quinolyl)-2-benzylidene-1,2-dihydroquinoline; 1,3-diphenyl-1-(2-quinolyl)acetone; dibenzyl ketone
