HETEROCYCLES [H]-FUSED TO 4-OXOQUINOLINE-3-CARBOXYLIC ACID. PART IX.(1) SYNTHESIS OF 2,6-DIOXOTETRAHYDRO-1H-PYRROLO[3,2-H]QUINOLINE-7-CARBOXYLIC ACID

作者：Zahra Jalal A^*; Al Jaber Hala I; El Abadelah Mustafa M; Abadleh Mohammed M

来源：Heterocycles, 2011, 83(9): 2165-2175.

DOI：10.3987/COM-11-12274

• 7-Carboxymethyl-8-nitroquinolone Derivative
• Reductive Lactamization
• Tricyclic Fluoroquinolone
• Oxindole Derivative
• SNAr Reaction

Interaction of deprotonated malonic esters with 7-chloro-8-nitro-4-oxoquinoline-3-carboxylate (1) gave the respective 7-[bis(alkoxycarbonyl)methyl] derivatives (2, 3) which were converted into the corresponding 7-(carboxymethyl)-8-nitro-4-oxoquinoline-3-carboxylic acid (4). Reductive lactamization of the latter furnished the target tetrahydro-2,6-dioxo-1H-pyrrolo-[3,2-h]quinoline-7-carboxylic acid (5). Both compounds 4 and 5 exhibited broad spectrum of high antibacterial activity against representatives of Gram-negative and Gram-positive bacteria classes, but were less potent than the reference ciprofloxacin.

• 出版日期2011-9-1