Design,two-directional synthesis,DFT study of new pyrimido[5,4-d]pyrimidine-2,8-dione derivatives

A facile two-directional synthesis of new pyrimido[5,4-d]pyrimidine-2,8-dione was reported via an efficient reaction of premade bis-aldehydes and 1-(2-amino-1,2-dicyanovinyl)-3-phenylurea in the presence of triethylamine as the base and Cu (II) as catalyst. As there is controversy about the formation of two types of products, that is, purine or pyrimidine ring containing compounds in the reaction of diaminomaleonitrile with isocyanates and aldehydes, the computational model chemistry has been employed to obtain new insight about this reaction and determining the dominant pathway of the process. Using DFT model, two alternative pathways have been explored and geometrical isomerization of central double bond has been considered. Accordingly, the evaluated energy barriers affirm the formation of six-membered pyrimidine ring as the major product in the presence of CuCl₂ as the catalyst and MeOH as solvent.