56149-65-6Relevant academic research and scientific papers
PREPARATION OF 3-SUBSTITUTED QUINOLINES. II. PREPARATION AND CYCLODEHYDRATION OF α-ALKYL- AND α-PHENYL-β-ARYLAMINOACROLEIN DERIVATIVES
Todoriki, Reiko,Ono, Machiko,Tamura, Shinzo
, p. 755 - 769 (2007/10/02)
α-Methyl-β-arylaminoacroleins were prepared by the hydrolysis of 2-methyl-1-arylamino-3-arylimino-1-propene derivatives. α-Ethyl- and α-phenyl-β-arylaminoacroleins were prepared by the reaction of arylamine and 2-substituted 1,1,3,3-tetraethoxypropane derivatives. 3-Methyl, 3-ethyl- and 3-phenylquinolines were obtained from α-methyl-, α-ethyl and α-phenyl-β-arylaminoacroleins on heating with aluminum bromide in good yields. α-Bromo-β-anilinoacrolein (9b) was prepared by the reaction of β-anilinoacrolein (6b) and N-bromosuccinimide.Reaction of 9b and aluminum bromide did not afford 3-bromoquinoline.
Thermolysis of Polyazapentadienes. Part 6. Gas-phase Cyclisation of 1,5-Diaryl-1,5-diazapentadienes: Mechanistic Aspects and some Synthetic Applications
McNab, Hamish,Murray, M. Elizabeth-Ann
, p. 1565 - 1568 (2007/10/02)
The mode of formation of quinolines by gas-phase pyrolysis of 1,5-diaryl-1,5-diazapentadienes is contrasted with the thermal behaviour of 1,2,5-triazapentadienes.The mechanism involves concerted ring closure followed by a rapid 1,5-hydrogen shift to give a 3,4-dihydroquinoline intermediate, e.g. (19) or (21).Subsequent aromatisation takes place by a stepwise, free-radical process.Methylquinolines (9), (10), (12), and (13) were obtained on a preparative scale by this method.
