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Communication | Regular issue | Vol 38, No. 4, 1994, pp.733-738
Published online, 1st January, 1970
DOI: 10.3987/COM-93-6640
Model Experiments for Acetylation of the Marine Sponge Purines Agelasimine-A and Agelasimine-B

Tozo Fujii,* Tohru Saito, Jun Chikazawa, Masashi Ohba, and Tadamasa Date

*Faculty of Pharmaceutical Scicences, Kanazawa University, 13-1 Takara-machi, Kanazawa 920-0934, Japan


Reaction of 7-benzyl-N6,3-dimethyladenine (1b) and 7-benzyl-1,2-dihydro-1,3-dimethyladenine (2b), selected as models for the marine sponge alkaloids agelasimine-A (1a) and agelasimine-B (2a), with acetic anhydride in pyridine have been studied. The product from 1b was the imidazole derivative (6b), whose structure was determined by an X-ray crystallographic analysis. The product from 2b was the N6-acetyl derivative (4b). On treatment with boiling H2O, 4b gave 7-benzyl-2,3-dimethylhypoxanthine (5b) and a compound presumed to be 11.