Synthesis of lin-Benzofervenulin, lin-Benzotheophylline, and lin-Benzocaffeine

Article abstract of DOI:10.1021/jo00321a035

The synthesis of 7,9-dimethylpyrimido<5,4-g>-1,2,4-benzotriazine-6,8(7H,9H)-dione (3) as the lin-benzo-separated analogue of fervenulin is reported in five steps from 7-chloro-2,4(1H,3H)-quinazolinedione.The preparation of lin-benzotheophylline (11) is described as arising from 1,3-dimethyl-7-hydrazino-6-nitro-2,4(1H,3H)-quinazolinedione (9) in a procedure originally designed to give 3.Methylation of 11 is shown to yield two products, one of which is lin-benzocaffeine (18).