The synthesis of “stretched-out” analogs of lumazine, 6,7-dimethyllumazine and 2-amino-5,6,7,8-tetrahydro-6,7-dimethyl-4-pteridinone

The synthesis of pyrazino2,3-g]quinazolin-2,4-(1H,3H)dione ( 4 ) and its 7,8-dimethyl derivative ( 5 ), as linear benzo-separated lumazines, is reported. Also described is the preparation of 2-amino-6,7,8,9-tetrahydro-7,8-dimethylpyrazino2,3-g]quinazolin-4-one ( 6 ), as a linear benzo-separated analog of a synthetic cofactor for phenylalanine hydroxylase. All of the syntheses began with ethyl 2,4,5-triaminobenzoate ( 8 ) and proceeded through the appropriate derivatives of ethyl 6-aminoquinoxaline-7-carboxylate ( 9, 10 , and 11 ) which were subsequently ring closed to 4, 5 , and 6 .