A route to functionalized pyrimidines from carbohydrates via amine-driven dehydrative ring transformations

A novel and expeditious synthetic protocol for functionalized pyrimidines using unprotected aldoses as biorenewable resources is reported. The synthesis involves aza-Michael addition of aromatic amines to aldose-derived 1,3-oxazin-2-ones(thiones) followed by dehydrative ring transformation to afford 4-polyhydroxyalkylpyrimidin-2-ones(thiones) in excellent yields. This is a one-pot Montmorillonite K-10 clay-catalyzed amine-driven process proceeding under solvent-free microwave irradiation conditions.