含硫黄ピリミド[5,4-d]ピリミジン化合物の合成研究(第4報)4,8-Dipiperidino-pyrimido[5,4-d]pyrimidine-2,6-disulfonyl Dichlorideとジエタノールアミンの反応によるDipyridamoleの生成機構

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The mechanism of dipyridamole (V) formation from 4,8-dipiperidinopyrimido[5,4-d]-pyrimidine-2,6-disulfonyl dichloride (IV) and diethanolamine was examined : Reaction of ^<14>Cdisu1fonamide (VI) with cold diethanolamine at 110-120°gave V. This reaction was thought to be an intramolecular rearrangement. Four compounds (VII, VIII, IX, X) were isolated as intermediates in the formation of V. The reaction of these compounds with diethanolamine gave V in a good yield. The reaction of sulfonamide compounds (VI, VII, IX) with a string base, such as sodium hydroxide solution or diethanolamine, gave aminoether compounds (VIII, X) by intramolecular rearrangement, and the effect of acid catalysis for the rate of intramolecular rearrangement of aminoether compounds was proved.
公益社団法人日本薬学会の論文
1976-05-25