Walid Fathalla, P. Pazdera
Sep 8, 2017
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Journal
Journal of Heterocyclic Chemistry
Abstract
A series of 1-[(4-hydroxy-2-oxo-1-phenyl-1,2-dihydroquinolin-3-yl)carbonyl]-4-(substituted) piperazines 3a–c and methyl 2-[(4-hydroxy-2-oxo-1-phenyl-1,2-dihydroquinolin-3-yl)carbonylamino] alkanoates 5a–d has been developed by the direct condensation of ethyl [4-hydroxy-2-oxo-1-phenyl-1,2-dihydro-3-quinoline] carboxylate 2 with N1-monosubstituted piperazine hydrochlorides or amino acid ester hydrochloride in the presence of triethyl amine. The quinolone amino acid esters 5a–d were the key intermediate for the preparation of a series of 1-[2-((4-hydroxy-2-oxo-1-phenyl-1,2-dihydroquinolin-3-yl)carbonylamino)alkylcarbony]-4-substituted piperazine derivatives 8–11 (a-d) via azide coupling method with amino acid ester hydrochloride.