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Paper | Regular issue | Vol 38, No. 9, 1994, pp.2009-2015
Published online, 1st January, 1970
DOI: 10.3987/COM-94-6761
Condensed as-Triazines: Synthesis of Imidazo[4,5-e]-as-triazine 1-Oxides (6-Azapurine 6-Oxides) as Guanine and Hypoxanthine Analogues

Dau-Chang Wei, Long-Chih Hwang, and Cherng-Chyi Tzeng*

*School of Chemistry, Kaohsiung Medical University, 100 Shin Chuen 1st Rd., Kaohsiung 80708, Taiwan, R.O.C.

Abstract

Imidazo[4,5-e]-as-triazine 1-oxides (6-azapurine 6-oxides), structurally related to guanine and hypoxanthine, have been prepared. Reaction of 5,6-diamino-3-methylsulfonyl-as-triazine 1-oxide (1) with hydrazine afforded 5,6-diamino-3-hydrazino-as-triazine 1-oxide (2) which was then oxidized with mercuric oxide to give 5,6-diamino-as-triazine 1-oxide (3). The 3-methylsulfonyl group of 1 was also replaced with liquid ammonia and methanolic ammonia respectively to give 3-amino (5) and 3-methoxy (6) derivatives. as-Triazine N-oxides were then cyclized with triethyl orthoformate (TEOF) to afford the title compounds.