Reaktionsgleichung
[F:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[C:4]([N+:9]([O-:11])=[O:10])[C:3]=1[OH:12].Cl[CH2:14][C:15](=[O:19])[C:16]([OH:18])=[O:17].ClCC(=O)C>>[F:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[C:4]([N+:9]([O-:11])=[O:10])[C:3]=1[O:12][CH2:14][C:15](=[O:19])[C:16]([OH:18])=[O:17]Komponenten
Versuchsvorschrift
3.9 g of 2,3-difluoro-6-nitrophenol and 3.0 g of chloropyruvic acid are reacted as described for chloroacetone in Example 8 of U.S. Pat. No. 4,382,892, to yield (2,3-difluoro-6-nitrophenoxy)-pyruvic acid. Catalytic hydrogenation (Pd/C or Raney Ni, room temperature) of the product yields in one step 7,8-difluoro-[1,4]benzoxazine-3-carboxylic acid, which is converted to its acid chloride and then is reacted first with triethylphosphite and next with diethylphosphite and a base, to form 7,8-difluoro-3-[hydroxy-bis(diethoxyphosphono)methyl]-[1,4]benzoxazine. Condensation of the latter with diethyl ethoxymethylidenemalonate, as in the above-mentioned patent, cyclization, and ester hydrolysis gives 9,10-difluoro-3-[hydroxy-bis(diethoxyphosphono)methyl]-7-oxo-2,3-dihydro-7H-pyrido[1,2,3-de][1,4]benzoxazine-6-carboxylic acid, which is finally reacted with 1-methylpiperazine to yield 9-fluoro-3-[hydroxy-bis(diethoxyphosphono)methyl]-10-(4-methyl-l-piperazyl)-7-oxo-2,3-dihydro-7H-pyrido[1,2,3-de][1,4]benzoxazine-6-carboxylic acid.
Quellen und Nachweise
- ORD-Eintrag
- ord-4aa9babee94b432390d4fa320718b898
- Quelldatensatz
- uspto-grants-1998_12
- Patentnummer
- US05854227
Verknüpfte Notizen
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