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项目整合精选>>>Ciprofloxacin hydrochloride, Bay-o-9867 monohydrate, Septocipro, Ciprenit, Velmonit, Cipro XR, Ciproxan, Sarf, Cetraxal, Ciprobay, Ciloxan, Ciflox, Cipro, Eni, Ciproxin, Oftacilox
Ciprofloxacin hydrochloride, Bay-o-9867 monohydrate, Septocipro, Ciprenit, Velmonit, Cipro XR, Ciproxan, Sarf, Cetraxal, Ciprobay, Ciloxan, Ciflox, Cipro, Eni, Ciproxin, Oftacilox
盐酸环丙沙星 环丙沙星 Chemical Name: 1-Cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-3-quinolinecarboxylic acid hydrochloride hydrate
CAS No. 86393-32-0, 85721-33-1 (free base, anhydrous)
项目整合开发状态: Launched-1986
项目研究机构: Bayer (Originator), Schering-Plough (Marketer), Alcon (Licensee), Esteve (Licensee), Salvat (Licensee), Vita (Licensee), National Institutes of Health (Codevelopment)
合成路线:The condensation of 2,4-dichloro-5-fluorobenzoyl chloride (I) with diethyl malonate (II) by means of magnesium ethoxide in ether gives diethyl 2,4-dichloro-5-fluorobenzoylmalonate (III),which is partially hydrolyzed and decarboxylated with p-toluenesulfonic acid water yielding ethyl 2,4-dichloro-5-fluorobenzoylacetate (IV).The condensation of (IV) with triethyl orthoformate (V) in refluxing acetic anhydride affords ethyl 2-(2,4-dichloro-5-fluorobenzoyl)-3-ethoxyacrylate (VI),which is treated with cyclopropylamine (VII) in ethanol to give ethyl 2-(2,4-dichloro-5-fluorobenzoyl)-3-cyclopropylaminoacrylate (VIII).The cyclization of (VIII) with NaH in refluxing dioxane yields 7-chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid (IX),which is finally condensed with piperazine (X) in hot DMSO.
📌 参考资料/链接：
参考文献标题:1-Cyclopropyl-6-fluoro-1,4-dihidro-4-oxo-7-piperazino-quinoline-3-carboxilic acids,process for their preparation and antibacterial agents containing them
文献作者:Grohe,K.; Zeiler,H.J.; Metzger,K.G.(Bayer AG)
参考来源:EP 0078362; JP 4253963; JP 58074667
📄 详细内容
合成路线:The condensation of 2,4-dichloro-5-fluorobenzoyl chloride (I) with diethyl malonate (II) by means of magnesium ethoxide in ether gives diethyl 2,4-dichloro-5-fluorobenzoylmalonate (III),which is partially hydrolyzed and decarboxylated with p-toluenesulfonic acid water yielding ethyl 2,4-dichloro-5-fluorobenzoylacetate (IV).The condensation of (IV) with triethyl orthoformate (V) in refluxing acetic anhydride affords ethyl 2-(2,4-dichloro-5-fluorobenzoyl)-3-ethoxyacrylate (VI),which is treated with cyclopropylamine (VII) in ethanol to give ethyl 2-(2,4-dichloro-5-fluorobenzoyl)-3-cyclopropylaminoacrylate (VIII).The cyclization of (VIII) with NaH in refluxing dioxane yields 7-chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid (IX),which is finally condensed with piperazine (X) in hot DMSO.
参考文献标题:Ciprofloxacin
文献作者:Serradell,M.N.; Castar,J.
参考来源:Drugs Fut 1984,9(3),179
合成路线:The condensation of 2,4-dichloro-5-fluorobenzoyl chloride (I) with diethyl malonate (II) by means of magnesium ethoxide in ether gives diethyl 2,4-dichloro-5-fluorobenzoylmalonate (III),which is partially hydrolyzed and decarboxylated with p-toluenesulfonic acid water yielding ethyl 2,4-dichloro-5-fluorobenzoylacetate (IV).The condensation of (IV) with triethyl orthoformate (V) in refluxing acetic anhydride affords ethyl 2-(2,4-dichloro-5-fluorobenzoyl)-3-ethoxyacrylate (VI),which is treated with cyclopropylamine (VII) in ethanol to give ethyl 2-(2,4-dichloro-5-fluorobenzoyl)-3-cyclopropylaminoacrylate (VIII).The cyclization of (VIII) with NaH in refluxing dioxane yields 7-chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid (IX),which is finally condensed with piperazine (X) in hot DMSO.
参考文献标题:Microwave assisted amination of quinolone carboxylic acids: An expeditious synthesis of fluoroquinolone antibacterials
文献作者:Reddy,P.G.; Baskaran,S.
参考来源:Tetrahedron Lett 2001,42(38),6775
产品链接: CAS No. 86393-32-0›› 产品链接: CAS No.85721-33-1››