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Communication | Regular issue | Vol 4, No. 10, 1976, pp.1659-1662
Published online, 1st January, 1970
DOI: 10.3987/R-1976-10-1659
A Dichotomy in the Intramolecular Cycloaddition of Aza Analogs of Hexatriene. Thermolysis and Photolysis of 6-Benzylideneamino-5-dimethylaminomethyleneamino-1,3-dimethyluracils

Fumio Yoneda,* Masatsugu Kiguchi, and Mitsuko Kawamura

*Faculty of Pharmaceutical Sciences, Kumamoto University, 5-1 Oe-hon-machi, Kumamoto 862-0973, Japan

Abstract

The 5-dimethylaminomethylene derivatives (II) resulting from the condensation of the 6-amino-5-benzylideneamino-1,3-dimethyluracils (I) with dimethylformamide diethylacetal underwent intramolecular cycloaddition by thermolysis in sulfolane to yield the respective 1,3-dimethyllumazine derivatives (III), while the photolysis of II in alcohol led to the formation of theophylline via another type of cycloaddition.