New Synthetic Approach to 8-Allyltheophylline

Article abstract of DOI:10.1007/BF00811849

The synthesis of 8-allyltheophylline (8) from 5,6-diamino-1,3-dimethyluracil (1) and 3-butenoic acid by Traube's method via 6-amino-5-(3-butenoylamino)-1,3-dimethyluracil (2) failed because an attempted alkaline cyclization of the intermediate 2 afforded (E)-8-(1-propenyl)-theophylline (3) under rearrangement of the terminal C=C bond.Therefore, the cyclodehydratation of 6-(3-butenylamino)-5-nitroso-1,3-dimethyluracil (7), available from 6-chloro-1,3-dimethyluracil (5) via 6-(3-butenylamino) derivative 6 has to be used for obtaining the required product 8. - Keywords: 8-Allyltheophylline; 8-(1-Propenyl)-theophylline; Rearrangement of the terminal C=C bond.