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The reactivity of oxygen-bridged Biginelli pyrimidines, such as 2,6-methano-1,3,5benzoxadiazocines, towards nitrogen nucleophiles such as hydrazine hydrate, N,Ndimethylhydrazine, and benzylamine was studied. While all these reagents caused opening of the oxygen-containing ring, only the reaction with hydrazine furnished the corresponding pyrazolopyrimidine and pyridopyrimidine condensation products. 1 H– 15 N HMBC correlation spectroscopy was used for structure confirmation.

Transformation of oxygen-bridged pyrimidines with nitrogen nucleophiles and characterization of resulting products