合成路线:1) The condensation of 2,4-dichloro-5-fluoro-benzoyl chloride (I) with diethyl malonate (II) by means of magnesium ethoxide gives diethyl 2,4-dichloro-5-fluorobenzoylmalonate (III),which is partially decarboxylated with p-toluenesulfonic acid yielding ethyl 2,4-dichloro-5-fluorobenzoylacetate (IV).The condensation of (IV) with triethyl orthoformate (V) by means of refluxing acetic anhydride affords ethyl 2-(2,4-dichloro-5-fluorobenzoyl)-3-ethoxyacrylate (VI),which is treated with cyclopropylamine (VII) in ethanol giving ethyl 2-(2,4-dichloro-5-fluorobenzoyl)-3-(cyclopropylamino)acrylate (VII).The cyclization of (VII) by means of NaH in refluxing dioxane yields 1-cyclopropyl-7-chloro-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid (IX),which is finally condensed with N-ethylpiperazine (X) by heating at 140 C in DMSO.
合成路线:2) The condensation of quinoline (IX) with piperazine (XI) by heating at 140 C as before gives 1-cyclopropyl-6-fluoro-7-(1-piperazinyl)-4-oxo-1,4-dihydroquinoline-3-3-carboxylic acid (XII),which is finally treated with ethyl iodide and triethylamine in hot DMF.
合成路线:3) The condensation of 2,4-dichloro-5-fluorobenzoyl chloride (I) with methyl 3-(cyclopropylamino)acrylate (XIII) gives methyl 2-(2,4-dichloro-5-fluoro-benzoyl)-3-(cyclopropylamino)acrylate (XIV),which is first cyclized with t-BuOK and then hydrolyzed to give compound (IX).
参考文献标题:Antimicrobial agent of quinolone-carboxylic acid b
文献作者:Grohe,K.; Petersen,U.; Kuck,K.-H.(Bayer AG)
参考来源:DE 3248507; US 4563459
合成路线:1) The condensation of 2,4-dichloro-5-fluoro-benzoyl chloride (I) with diethyl malonate (II) by means of magnesium ethoxide gives diethyl 2,4-dichloro-5-fluorobenzoylmalonate (III),which is partially decarboxylated with p-toluenesulfonic acid yielding ethyl 2,4-dichloro-5-fluorobenzoylacetate (IV).The condensation of (IV) with triethyl orthoformate (V) by means of refluxing acetic anhydride affords ethyl 2-(2,4-dichloro-5-fluorobenzoyl)-3-ethoxyacrylate (VI),which is treated with cyclopropylamine (VII) in ethanol giving ethyl 2-(2,4-dichloro-5-fluorobenzoyl)-3-(cyclopropylamino)acrylate (VII).The cyclization of (VII) by means of NaH in refluxing dioxane yields 1-cyclopropyl-7-chloro-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid (IX),which is finally condensed with N-ethylpiperazine (X) by heating at 140 C in DMSO.
合成路线:2) The condensation of quinoline (IX) with piperazine (XI) by heating at 140 C as before gives 1-cyclopropyl-6-fluoro-7-(1-piperazinyl)-4-oxo-1,4-dihydroquinoline-3-3-carboxylic acid (XII),which is finally treated with ethyl iodide and triethylamine in hot DMF.
合成路线:3) The condensation of 2,4-dichloro-5-fluorobenzoyl chloride (I) with methyl 3-(cyclopropylamino)acrylate (XIII) gives methyl 2-(2,4-dichloro-5-fluoro-benzoyl)-3-(cyclopropylamino)acrylate (XIV),which is first cyclized with t-BuOK and then hydrolyzed to give compound (IX).
参考文献标题:Enrofloxacin
文献作者:Castar,J.; Prous,J.
参考来源:Drugs Fut 1988,13(4),305
产品链接: CAS No. 93106-60-6››