Quinazolines. XXIV. The Synthesis of 2,4-Diazatetra-cyclo[7,3,1,1^7,11,0^1,6]tetradecanes(Adamantano [1,2-d]pyrimidines)

Abstract

The syntheses of 6-hydroxy-2,4-Diazatetracyclo[7,3,1,1^7,11,0^1,6]tetradecan-3-iminium (4) picrate and related compounds starting from 2-oxoadamantane-1-carbonyl chloride (5) are described. In preliminary biological evaluation it was found that the most toxic (M.L.D. values for mice) adamantane derivative, 3,5 diazatetracyclo[7,3,1,1^7,11,0^1,6]tetradecane-2,4-dione (76 mg kg^-1), was much less toxic than tetrodotoxin (0.013 mg kg^-1).