58346-55-7Relevant academic research and scientific papers
Studies on organometallic compounds. VII. Reaction of di-tert-butyl dicarbonate with α-trialkylstannyl derivatives of pyridine, quinoline, and isoquinoline
Yamamoto,Ouchi,Tanaka
, p. 916 - 919 (2007/10/02)
Di-tert-butyl dicarbonate was found to be effective for direct introduction of a tert-butoxycarbonyl group at the α-position of the pyridine nucleus via the trialkylstannyl group; reaction of α-trialkylstannyl derivatives of pyridine, quinoline, and isoquinoline with di-tert-butyl dicarbonate gave the corresponding α-tert-butoxycarbonyl derivatives in good yields, although small amounts of a variety of by-products were formed except in the case of pyridine.
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
