Nucleophilic addition reactions of [1,2,5]oxadiazolo[3,4-d] pyrimidine 1-oxides (pyrimidofuroxans)
Abstract
5-Dimehtylamino-[1,2,5]oxadiazolo[3,4-d]pyrimidine 1-oxide reacts preferentially at the C-7 Position of the pyrimidine ring with nucleophilic reagents (water, alcohols, amines, and the hydride ion) giving readily isolable covalent adducts in which the furoxan ring remains intact but in the case of the water adduct this ring can be opened oxidatively under mild conditions to afford the corresponding 5,6-dinitropyrimidin-4(3H)-one derivative.