Preparation of 2-phenyl-2-hydroxymethyl-4-oxo-1,2,3,4-tetrahydroquinazoline and 2-methyl-4-oxo-3,4-dihydroquinazoline derivatives formation

Article abstract of DOI:10.1002/jhet.5570370427

The cyclization of phenacyl anthranilate has been studied with the aim to develop the synthesis of 2-(2'-aminophenyl)-4-phenyloxazole. However, a different course of the reaction than expected was observed. 2-Phenyl-2-hydroxymethyl-4-oxo-1,2,3,4-tetrahydroquinazoline (3a) was formed by the reaction of phenacyl anthranilate (2) with ammonium acetate under various conditions. 3-Hydroxy-2-phenyl-4(1H)-quinolinone (4) arose by heating compound 3a in acetic acid. The same compound was obtained by melting compound 3a, but the yield was lower. Different types of products resulted in the reaction of compound 3a with acetic anhydride. Under mild conditions acetylated products 2-acetoxymethyl-2-phenyl-4-oxo-1,2,3,4-tetrahydroquinazoline (7a) and 2-acetoxymethyl-3-acetyl-2-phenyl-4-oxo-1,2,3,4-tetrahydroquinazoline (8) were prepared. If the reaction was carried out under reflux of the reaction mixture, molecular rearrangement took place to give cis and trans 2-methyl-4-oxo-3-(1-phenyl-2-acetoxy)vinyl-3,4-dihydroquinazolines (9a and 9b). All prepared compounds have been characterised by their ¹H, ¹³C and ¹⁵N NMR spectra, IR spectra and MS.