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合成 (±)-9,10-二氟-3-(羟甲基)-7-氧代-2,3-二氢-7 H-吡啶并[1.2,3-de]-1,4-苯并(口恶)嗪-6羧酸乙酯(Ⅰ)是合成外消旋氧氟沙星(ofloxacin)的中间体。Ⅰ与3,5-二硝基苯甲酰氯(Ⅱ)反应得外消旋的酯(Ⅲ),再经高压液相层析分得左旋光学异构体(Ⅳ),后者用含醇的碳酸氢钠水溶液进行部份水解,即得到左旋体醇(Ⅴ),再在DMF中与亚磷酸三苯酯甲基碘化物反应得相应的左旋碘甲基衍生物(Ⅵ)。Ⅵ在乙醇中用三丁基氢化锡还原和水解得化合物Ⅶ,后者在DMSO中于120℃下与N-甲基哌嗪(Ⅷ)反应得本品。
Synthesis of (±) -9,10-difluoro-3- (hydroxymethyl) -7-oxo-2,3-dihydro-7 H -pyrido [1.2,3-de] -1,4-benzene Ethyl (ox e) oxazine-6 carboxylate (Ⅰ) is an intermediate in the synthesis of ofloxacin. (III) with 3,5-dinitrobenzoyl chloride (II) followed by high pressure liquid chromatography gave the L-optical isomer (IV), which was treated with alcohol The partial hydrolysis with aqueous sodium bicarbonate gives the levonorol (V), which is then reacted with triphenyl phosphite in the DMF to give the corresponding L-iodomethyl derivative (VI). Ⅵ Reduction and hydrolysis with tributyltin hydride in ethanol yields compound VII which reacts with N-methylpiperazine (VIII) in DMSO at 120 ° C.