Green synthesis of chromeno-pyrimidine derivatives – Part I

Abstract

Two different chromeno-pyrimidine derivatives were synthetized in the ionic liquid catalyzed reaction of barbituric acid and substituted salicylaldehydes. The product 5-(7-bromo- 2,4-dioxo-1,3,4,5-tetrahydro-2H-chromeno[2,3-d]pyrimidin-5-yl)pyrimidine-2,4,6(1H,3H,5H)-trione (CP-1) was obtained in the reaction of barbiruric acid and 5-bromo-2-hydroxybenzaldehyde. The second new product 8,9-dihydroxy-2H-chromeno[2,3-d]pyrimidine-2,4(3H)-dione (CP-2) was yielded in the reaction between barbituric acid and 2,3,4-trihydroxybenzaldehyde. These products were isolated in moderate to good yield after 3h reflux in mixture of water: ethanol (1:1v/v) and in presence 20 mol% of catalyst – diethanolammonium chloroacetate. The structure of obtained products was confirmed using 1H NMR, 13C NMR, and IR spectroscopy methods.