23545-77-9Relevant articles and documents
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.