A Novel One-Pot Synthesis of Substituted Quinolines

A synthesis of quinoline derivatives is described via reaction between ethyl bromopyruvate (=ethyl 3-bromo-2-oxopropanoate), acetylenedicarboxylate, and isatin (=1H-indole-2,3-dione) in the presence of NaH as a base. Also, these reactions were performed without ethyl bromopyruvate. The reaction in the presence of ethyl bromopyruvate provides regioselectively a quinoline with the ethyl ester group in 4-position. In the absence of ethyl bromopyruvate, the reaction leads to functionalized quinolines with the same ester groups in 2-, 3-, and 4-positions.