Synthesis of new 3H-chromeno[2,3-d]pyrimidine-4,6(5H,7H)-diones via the tandem intramolecular Pinner/Dimroth rearrangement

Abstract

The reaction of 2-amino-4-aryl-7,7-dimethyl-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carbonitriles with excess aliphatic carboxylic acids in the presence of phosphoryl chloride (POCl3) afforded new 2-alkyl-5-aryl-8,8-dimethyl-8,9-dihydro-3H-chromeno[2,3-d]pyrimidine-4,6(5H,7H)-diones in high yields. The suggested mechanism involves a tandem intramolecular Pinner/Dimroth rearrangement. The synthesized compounds were characterized by infrared (IR), proton nuclear magnetic resonance (1H NMR), carbon-13 nuclear magnetic resonance (13C NMR) and elemental analysis.