208664-59-9Relevant academic research and scientific papers
Gas-phase cyclisation reactions of 1-(2-arylaminophenyl)alkaniminyl radicals
Leardini, Rino,McNab, Hamish,Nanni, Daniele,Parsons, Simon,Reed, David,Tenan, Anton G.
, p. 1833 - 1838 (1998)
Flash vacuum pyrolysis (FVP) of the oxime ethers 9-11 at 650°C (10-2-10-3 Torr) gives products such as the nitrile 17, carbazoles 19 and 20 and acridines 18 and 21 derived from the corresponding iminyl radicals 13-15. The mechanism proposed for the formation of the acridines involves a key hydrogen abstraction by the iminyl of the adjacent N-H atom. When this route is blocked by an N-methyl group, as in 12, alternative cyclisations ensue, yielding the dihydroquinazoline 26 (via another hydrogen abstraction process) and the benzimidazole 25 (via an iminyl-imidoyl interconversion).
