2015Journal of applied chemical research.Requires access

SYNTHESIS AND CHARACTERIZATION OF NOVEL 4-OXO-1, 4-DIHYDROQUINOLINE-3-CARBOXAMIDE DERIVATIVES FROM DIAZOMETHANE AND HCL (G)

Navabeh Nami, Kazemi Seyed Marziyeh

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Abstract

Reaction of thionyl chloride with 7-chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4- oxoquinoline-3-carboxylic acid 1 gave acid chloride 2. Compound 2 was reacted with glycine and D-glutamic acid to afford 2-(7-chloro-1-cyclopropyl-6-fluoro-4-oxo-1,4- dihydroquinoline-3-carbonyl) aminopantandioicacid 3a and 2-(7-chloro-1-cyclopropyl-6- fluoro -4- oxo-1,4-dihydroquinoline-3-carbonyl)aminoaceticacid 3b. These compounds were changed to chloromethyl ketone derivatives 5a-b from diazomethane and then HCl (g)in dry diethyl ether.

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What this paper is about

Reaction of thionyl chloride with 7-chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4- oxoquinoline-3-carboxylic acid 1 gave acid chloride 2. Compound 2 was reacted with glycine and D-glutamic acid to afford 2-(7-chloro-1-cyclopropyl-6-fluoro-4-oxo-1,4- dihydroquinoline-3-carbonyl) aminopantandioicacid 3a and 2-(7-chloro-1-cyclopropyl-6- fluoro -4- oxo-1,4-dihydroquinoline-3-carbonyl)aminoaceticacid 3b. These compounds were changed to chloromethyl ketone derivatives 5a-b from diazomethane and then HCl (g)in dry diethyl ether.

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Available abstract

Reaction of thionyl chloride with 7-chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4- oxoquinoline-3-carboxylic acid 1 gave acid chloride 2. Compound 2 was reacted with glycine and D-glutamic acid to afford 2-(7-chloro-1-cyclopropyl-6-fluoro-4-oxo-1,4- dihydroquinoline-3-carbonyl) aminopantandioicacid 3a and 2-(7-chloro-1-cyclopropyl-6- fluoro -4- oxo-1,4-dihydroquinoline-3-carbonyl)aminoaceticacid 3b. These compounds were changed to chloromethyl ketone derivatives 5a-b from diazomethane and then HCl (g)in dry diethyl ether.

Key concepts: Diazomethane, Thionyl chloride, Chemistry, Ketone, Diethyl ether, Medicinal chemistry, Ether, Carboxamide

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SYNTHESIS AND CHARACTERIZATION OF NOVEL 4-OXO-1, 4-DIHYDROQUINOLINE-3-CARBOXAMIDE DERIVATIVES FROM DIAZOMETHANE AND HCL (G) — Research Paper | ScholarLens