Efficient Synthesis of New Pyrimido[5′,4′:5,6]pyrano[2,3-d]pyrimidine-2,4,6(1H,3H)-triones via the Tandem Intramolecular Pinner–Dimroth Rearrangement, and Their Antibacterial Activity

Abstract

Synthesis of new 8-alkyl-5-aryl-1,3-dimethyl-5,7-dihydro-2H-pyrimido[5′,4′:5,6]pyrano[2,3-d]- pyrimidine-2,4,6(1H,3H)-triones by the high yield reaction of 7-amino-5-aryl-1,3-dimethyl-2,4-dioxo-1,3,4,5- tetrahydro-2H-pyrano[2,3-d]pyrimidine-6-carbonitriles with aliphatic carboxylic acids in the presence of POCl3 is presented. It is probable that synthesis of these new products proceeds via the tandem intramolecular Pinner–Dimroth rearrangement. The products are characterized by FT-IR, ¹H, and ¹³C NMR spectra and evaluated for their antibacterial activity against gram +ve bacteria (Staphylococcus aureus and Staphylococcus epidermidis) and gram–ve bacteria (Escherichia coli and Pseudomonas aeruginosa) using the disc diffusion method.