Collect. Czech. Chem. Commun. 1988, 53, 319-328

1,3-Dipolar cycloaddition reactions of 7-alkenyl- or 7-alkynyl-8-azidomethyltheophyllines

Dušan Heseka, Alfonz Rybára, František Považanecb, Augustin Martvoňa and Jaroslav Kováčb

a Drug Research Institute, 900 01 Modra
b Department of Organic Chemistry Slovak Institute of Technology, 812 37 Bratislava


8-Azidomethyltheophillines XI-XIV, containing dipolarophilic alkenyl or alkynyl (i.e. allyl, 2-butenyl, cinnamyl, and 2-propynyl) groups in position 7, undergo thermally induced 1,3-dipolar intramolecular cycloaddition under formation of 7-substituted 1,3-dimethyl-2,4-dioxo-1,2,3,4,6,6a,7,11-octahydro(1,2,3)triazolo[1’,5’:1,2]pyrazino[5,4-f]purines XV-XVII and 1,3-dimethyl-2,4-dioxo-1,2,3,4,6,11-hexahydro(1,2,3)triazolo[1’,5’:1,2]pyrazino[5,4-f]purine (XVIII), respectively. The compounds were synthesized starting from 8-hydroxymethyltheophilline (I) which was alkylated to give 7-alkenyl- and 7-alkynyl-8-hydroxymethyltheophillines III-VI and these were converted into the corresponding 8-halogenomethyl derivatives VII-X by treatment with thionyl chloride or phosphorus tribromide. Reaction of VII-X with sodium azide afforded the 8-azidomethyl derivatives XI-XIV.