96818-15-4Relevant academic research and scientific papers
Intramolecular Reactions of N-Nitrenes: Oxidation of 3-Amino-2-(2,4-dimethoxyphenylethyl)quinazolin-4(3H)-ones
Atkinson, Robert S.,Gawad, Nagwa A.
, p. 335 - 340 (2007/10/02)
Oxidation of the N-aminoquinazolones (5) and (6) gave the 1H-azepines (7) and (10) respectively.Boat-to-boat flipping of the azepine ring in compound (7) is slow on the n.m.r. time-scale even at 140 deg C.Heating of compound (10a) in chlorobenzene at 135 deg C brings about interconversion with the stereoisomer (10b) with a minimum free energy barrier of 30 kcal mol -1.Possible reasons for this high barrier to azepine ring inversion are examined.
