Utilization of Organoselenium Compounds. II. Reaction of Fused Isoselenazoles with Alkylamines(Organic,Chemical)

概要

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A facile conversion of the methyl group of 5-amino-6-methyl-3-phenyl-4(3H)-pyrimidinone (1) or 4-aminoautipyrine (5) to an alkyliminomethyl group by isoselenazole ring formation followed by reaction with alkylamines was carried out. 7-Oxo-6-phenyl-6H-isoselenazolo[4,3-d]pyrimidine (2), which was obtained from 1 and selenium dioxide, was reacted with alkylamines, such as n-propylamine, isopropylamine and 3-methoxypropylamine, to give 6-alkyliminomethyl-5-amino-3-phenyl-4(3H)-pyrimidinones (3a-d) in 47-58% yields. Treatment of 3a-d with silica gel gave 5-amino-6-formyl-3-phenyl-4(3H)-pyrimidinone (4) in 9l% yield. Similarly the reaction of 5,6-dihydro-4-methyl-6-oxo-5-phenyl-4H-pyrazolo[4,3-c]isoselenazole (6) with alkyiamincs gave 3-alkyliminomethyl-4-amino-1-phenyl-3-pyrazolin-5-ones (7a-f) in 50-97% yields.
社団法人日本薬学会の論文
1987-01-25