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.
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