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Communication | Special issue | Vol 11, No. 1, 1978, pp.247-252
Published online, 1st January, 1970
DOI: 10.3987/S(N)-1978-01-0247
Formation of 1,3-Dimethyllumazine-6-aldoxime by a Novel Cyclization Reaction

Herbert Fuchs and Wolfgang Pfleiderer*

*Fachbereich Chemi, Universität Konstanz, Postfach 7733, D-7750 Konstanz, Germany

Abstract

Nitrosation of 6-allylamino-1,3-dimethyluracil (1) in aqueous solution caused a novel ring closure forming 1,3-dimethyllumazine-6-aldoxime (5) whereas the reaction in aprotic solvents led to 8-vinyl-theophylline (11). 1,3-Diphenyl- (2), 1-methyl- (3) and 1-benzyl-6-allylaminouracil (4) react normally with nitrosation at C-5 followed by cyclization on heating to the corresponding 8-vinyl-xanthines 12 - 14.