Pyrimidine Derivatives and Related Compounds. XLVI. Thermal and Photochemical Transformation of 5-Substituted 6-Azido-1,3-dimethyluracils into Fused Pyrimidines such as Isoxazolo [3,4-d] pyrimidines, Pyrazolo [3,4-d]-pyrimidines, and Pyrimido [4,5-d]-[1,2

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Thermolysis and photolysis of 6-azido-1,3-dimethyluracils possessing certain substituents (formyl, benzoyl, hydrazonomethyl, phenyl, and benzyl groups) at the 5-position provided new methods for the preparation of fused pyrimidines. Irradiation and heating of 5-formyl-and 5-benzoyl-6-azidouracils (3 and 7) led to the formation of isoxazolo [3,4-d] pyrimidines (4 and 8). 2-(Substituted amino) pyrazolo [3,4-d] pyrimidines (14) were conveniently prepared by the reaction of 6-chloro-5-hydrazonomethyl-1,3-dimethyluracils (12) with sodium azide, followed by thermolysis of the resulting 6-azides. Upon thermolysis and photolysis of 5-phenyl-and 5-benzyl-6-azidouracils (16 and 19), pyrimido [4,5-b] indole (17) and pyrimido [4,5-b] quinoline (10) were obtained, respectively. Cyclization of 3 using triethyl phosphite and triphenylphosphine resulted in the formation of a new ring system, pyrimido [4,5-d] [1,2,3] triazine (5).
社団法人日本薬学会の論文
1983-11-25