Heterocyclic studies. Part XXXV. Cleavage of fervenulin and 3-methylfervenulin by nucleophiles
Abstract
Treatment of fervenulin {6,8-dimethylpyrimido[5,4-e]-as-triazine-5,7(6H,8H)-dione} and 3-methylfervenulin with primary amines gave 6-(3-alkyl-1-methylureido)-5-methylcarbamoyltriazines by attack at position 7 and cleavage of the 6,7-bond. Reactions with hydrazine and 1,1-dimethylhydrazine similarly gave triazin-6-ylsemicarbazides. Fervenulin and methylhydrazine gave 5,6-diamino-1,3-dimethyluracil and an unknown compound by cleavage of the triazine ring. The 6-(1-methyl-3-alkylureido)-5-methylcarbamoyltriazines were converted by cold nitrous acid into open-chain compounds. 1H N.m.r., mass, and u.v. spectra are tabulated and discussed.