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Communication | Regular issue | Vol 9, No. 11, 1978, pp.1571-1576
Published online, 1st January, 1970
DOI: 10.3987/R-1978-11-1571
Synthesis of 1,6-Dimethylpyrimido[4,5-c]pyridazine-5,7-(1H,6H)-dione (4-Deazatoxoflavin) Derivatives and Their Use in the Oxidation of Alcohols

Fumio Yoneda,* Masatsugu Higuchi, Mitsuko Kawamura, and Yoshihiro Nitta

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


Treatment of 3-methyl-6-(1-methylhydrazino)uracil (I) with phenacyl bromides afforded the corresponding 3-aryl-1,6-dimethylpyrimido[4,5-c]pyridazine-5,7 (1H,6H)-diones (3-aryl-4-deazatoxoflavins) (IIa-c) and 3-aryl-1,7-dimethyl-6,8-dioxo-1,4,6,7,8-pentahydropyrimido[4,3-c]-as-triazines (IIIa-c). The reaction of arylaldehyde N-methyl-N-(3-methyluracil-6-yl)hydrazones (IVa-e) with triethyl ortho-formate in DMF also gave the respective 4-deazatoxoflavins (IIa-e) .
3-Phenyl-4-deazatoxoflavin (IIa) thus obtained oxidized alcohols under alkaline conditions in the dark to yield the corresponding carbonyl compounds, while it is itself hydrogenated to 4,8-dihydro-3-phenyl-4-deazatoxoflavin (V).