16348-32-6Relevant academic research and scientific papers
A New type of Dimroth Rearrangement: Formation of 1,2-Dihydro-3H-quinazolone 4-Oximes from 4-Amino-1,2-dihydroquinazoline 3-Oxides
Korbonits, Dezsoe,Kolonits, Pal
, p. 2163 - 2168 (2007/10/02)
Contrary to earlier claims the primary product of the reaction of aldehydes and o-aminobenzamide oxime is, irrespective of the aldehyde, always a 4-amino-1,2-dihydroquinazoline 3-oxide.Thermolysis of 1-unsubstituted 2-substituted quinazoline 3-oxides (5) in solution or in melt gives rise, by a new type of Dimroth rearrangement, to the isomeric 1,2-dihydro-4-quinazolone oximes (6), while the 1-benzyl 2-unsubstituted analogue (9j) yields, presumably by an addition-elimination ring transformation coupled with oxidation, a quinoidal quinazolone 4-oxime (17).
