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Short Paper | Regular issue | Vol 83, No. 9, 2011, pp.2165-2175
Published online, 20th July, 2011
DOI: 10.3987/COM-11-12274
Heterocycles [h]-Fused to 4-Oxoquinoline-3-carboxylic Acid. Part IX. Synthesis of 2,6-Dioxotetrahydro-1H-pyrrolo[3,2-h]quinoline-7-carboxylic Acid

Jalal A. Zahra,* Hala I. Al-Jaber, Mustafa M. El-Abadelah, and Mohammed M. Abadleh

*Chemistry Department, Faculty of Science, The University of Jordan, Amman 11942, Jordan

Abstract

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.