Irloxacin, E-3432
伊洛沙星Chemical Name: 1-Ethyl-6-fluoro-4-oxo-7-(1-pyrrolyl)-1,4-dihydroquinoline-3-carboxylic acid
CAS No. 91524-15-1
项目整合开发状态: Phase III
项目研究机构: Esteve (Originator), Provesan (Originator)
合成路线:The reduction of 4-fluoro-3-nitroaniline (I) with SnCl2.2H20 in concentrated aqueous HCl gives 4 fluoro-m-phenylenediamine (II),which is condensed with diethyl ethoxymethylenemalonate (III) in refluxing ethanol to afford diethyl 4-fluoro-3-aminoanilinomethylenemalonate (IV).The cyclization of (IV) by means of acetic anhydride in diphenyl oxide at 250 C yields ethyl 7-acetamido-4-hydroxy-6-fluoroquinoline-3-carboxylate (V),which is alkyiated with ethyl bromide and NaOH in refluxing ethanol to give 7-amino-6-fluoro-1-ethyl-1,4 dihydro-4-oxoquinoline-3-carboxylic acid (VI).Finally,this compound is condensed with 2,5-dimethoxytetrahydrofuran (VII) in hot acetic acid.
📌 参考资料/链接：
参考文献标题:7-(1-Pyrrolyl) derivs.of 1-ethyl-1,4-dihydro-4-oxoquinoline-3-carboxylic acids and 1-ethyl-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acids and their use as antimicrobial agents
文献作者:Esteve Soler,J.(Provesan SA)
参考来源:EP 0134165; FR 2548664; FR 2559484; US 4552882
📄 详细内容
合成路线:The reduction of 4-fluoro-3-nitroaniline (I) with SnCl2.2H20 in concentrated aqueous HCl gives 4 fluoro-m-phenylenediamine (II),which is condensed with diethyl ethoxymethylenemalonate (III) in refluxing ethanol to afford diethyl 4-fluoro-3-aminoanilinomethylenemalonate (IV).The cyclization of (IV) by means of acetic anhydride in diphenyl oxide at 250 C yields ethyl 7-acetamido-4-hydroxy-6-fluoroquinoline-3-carboxylate (V),which is alkyiated with ethyl bromide and NaOH in refluxing ethanol to give 7-amino-6-fluoro-1-ethyl-1,4 dihydro-4-oxoquinoline-3-carboxylic acid (VI).Finally,this compound is condensed with 2,5-dimethoxytetrahydrofuran (VII) in hot acetic acid.
参考文献标题:Irloxafin
文献作者:Prous,J.; Castar,J.
参考来源:Drugs Fut 1986,11(10),839
产品链接: CAS No. 91524-15-1››