Amadori rearrangement of N-glucosides of 6-substituted 3-amino-2-aryl-4(3H)-quinazolinones

Amadori rearrangement of N-glucosides of 6-substituted 3-amino-2-aryl-4(3H)-quinazolinones has been carried out by the condensation of equimolecular amounts of D-glucose and oxalate of 6-substituted 3-amino-2-aryl-4-(3H)-quinazolinones (1a-f) in boiling methanol. These compounds can also be obtained by heating the N-glucosides of 6-substituted 3-amino-2-aryl-4(3H)-quinazolinones (2a-f) in absolute methanol in the presence of dry oxalic acid. The products obtained are characterized by IR, 1(H) NMR, C-13 NMR and mass spectral data and elemental analyses.