Organic Reactions in “Green Surfactant”: An Avenue to Bisuracil Derivative

An environmentally benign and chemoselective nucleophilic addition of 6-[(dimethylamino)­methyleneamino]-1,3-dimethylpyrimidine-2,4­(1<i>H</i>,3<i>H</i>)-dione with aldehydes (aromatic, aliphatic, and heterocyclic) using a “green surfactant” isolated from P. aeruginosa OBP1 in water at room temperature is described. In this protocol, products (i.e., bisuracils) were obtained in moderate to good yields. Ketones failed to provide any product(s). The biosurfactant is easily recyclable. The structures of the products (i.e., bisuracils) were established using various spectroscopic techniques, elemental analysis, and single-crystal X-ray analysis. Amide-iminol tautomerism in the product is detected by NMR spectroscopy and conclusively supported by single-crystal X-ray analysis