a b c d e Ausgehend von o-Halogenbenzoylchloriden 4 und offenkettigen sckundaren Enaminen 5 wird eine neue Synthese von 4-Chinolon-3-carbonsluren 12 beschrieben. Durch Umsetzung von 7-Halogcnchinolon-3-carbonsiuren 12ak rnit aliphalischen Aminen 14 werden antibakteriell hochwirksame 7-Aminochinolon-3-carbonsiiurea 15 erhaken. Das Spitzenprodukt der 1-Cyclopropylreihe. ..Ciprofloxacin" (Ha), wird als Breitband-chemotherapeutikum entwickelt. 29 Cydoaracylntioa of lih.minee Lsyathe!& of 4-QainObS cprboxylk Acids Starting with o-halobenzoyl chlorides 4 and open-chain secondary enamines 5, a new synthesis of 4-quinolone-3-carboxylic acids 12 is described. The reaction of 7-haloquinolone3-carboxyIic acids 12.-k with aliphatic amines 14 produces highly active antibacterial 7-aminoquinolon~-3-carcarboxylic acids 15. The main product of the l-cyclopropyl series, "ciprofloxacin" (15a), is being developed as a broad-spectrum chemotherapeutic agent.Base wurde lediglich o-Brombenzamid isoliert'). Die analoge Reaktion der primaren Enamine 1 rnit 2-Chlor-hitrobenzoylchlorid (2) fuhrt zunachst in guter Ausbeute zu den N-Acylierungsprodukten 3, die rnit verdunnter Schwefelsaure zu 2-Chlor-hitrobenzamid hydrolysieren. 6 4,5,6 1 X' X2 X3 X4 X5 R' R2 Liebigs Ann. Chem. 1987, 29-37 0 VCH Verlagsgesellschaft mbH, D-6940 Weinheim, 1987 0170-2041/87/0101-0029 $ 02.50/0 3 b 'H-NMR (CDCI,): S = 12.8 (NH), 5.5 (olef. CH), 2.2 und 2.5 (2 CH3-Signale), 7.5 und 8.5 (3 aromat. H). -IR (KBr): 1695,
~ ~ ~~ ~ ~~ Die Herstellung von 2-Amino-4-oxo-4H-chromen-3-carbaldehyd 4 aus 4-0xo-4H-chromen-3carbaldehyd 1 und seine Umsetzungen zu Pyrimidinochromenonen 5, Pyridinochromenonen 6, 7 und 2-Amino-4-oxo-4H-chromen-3-carbonitril 10 werden beschrieben. Reactions of 4-0xo-4H-chromene-3-carbaldehyde, I. -Synthesis and Reactions of 2-Amino-
4-0~0-4H-chromene-3-carbaldehydeThe preparation of 2-amino-4-oxo-4H-chromene-3-carbaldehyde 4 from 4-0x0-4H-chromene-3-carbaldehyde 1 and its reactions to give pyrimidinochromenones 5, pyridinochromenones 6, 7 and 2-amino-4-oxo-4H-chromene-3-carbonitrile 10 are described.
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