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SYNTHESIS AND ANALGESIC ACTIVITY OF BIS(3,4-DIHYDROQUINOXALIN-2(1H)-ONE) AND BIS(3,4-DIHYDRO-2H-1,4-BENZOXAZIN-2-ONE) DERIVATIVES

Иван Вячеславович Кулаков
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Abstract


An ester condensation between 3,5-diacetyl-2,6-dimethylpyridine and an excess of diethyl oxalate was used for the preparation of 4,4'-(2,6-dimethylpyridine-3,5-diyl)bis(2-hydroxy-4-oxobut-2-enoate). The synthesized hydroxyester was shown to readily react with оphenylenediamine and о-aminophenol with the formation of bis(3,4-dihydroquinoxalin-2(1H)-one) and bis(3,4-dihydro-2H-1,4-benzoxazin-2-one) derivatives, which showed superior in vivo analgesic activity compared to the reference drug, metamizole sodium.

 


Keywords


3,5-diacetyl-2,6-dimethylpyridine, 3,4-dihydro-2H-1,4-benzoxazin-2-one, 3,4-dihydroquinoxalin-2(1H)-one, analgesic activity, X-ray structural analysis.

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Latvian Institute of Organic Synthesis - Aizkraukles iela, 21, Riga, LV-1006, Latvia - hgs@osi.lv