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Communication | Special issue | Vol 77, No. 2, 2009, pp.849-854
Published online, 16th October, 2008
DOI: 10.3987/COM-08-S(F)111
The Facile Synthesis of 6-Azapurines by Transformation of Toxoflavins (7-Azapteridines)

Tomohisa Nagamatsu,* Jun Ma, and Fumio Yoneda

*Graduate School of Medicine, Dentistry and Pharmaceutical Sciences, Okayama University, 1-1-1 Tsushima-naka, Okayama 700-8530, Japan

Abstract

This paper describes a reliable and facile synthesis of 6-azapurines (1,5-dimethyl-1H-imidazo[4,5-e][1,2,4]triazin-6(5H)-ones) by treatment of toxoflavins (7-azapteridines) with 10% aqueous sodium hydroxide at 5–25 °C along with a benzilic acid type rearrangement, followed by decarboxylation and oxidation by air. Furthermore, heating the 6-azapurines in 10% ethanolic sodium hydroxides afforded the corresponding 1,2,4-triazine-5,6(1H,4H)-diones to be caused by ring fission of the imidazole of 6-azapurines.