Monatshefte fur Chemie p. 565 - 570 (1994)
Update date:2022-08-03
Topics:
Rybar, A.
Alfoeldi, J.
Smondrkova, I.
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.
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