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. Author manuscript; available in PMC: 2021 Jul 29.
Published in final edited form as: J Med Chem. 2015 May 26;58(11):4610–4623. doi: 10.1021/acs.jmedchem.5b00159

Scheme 1. Synthetic Route to Quinolinonyl DKAs 10a–aa and 11a–aaa.

Scheme 1.

aReagents and conditions: (a) ethyl orthoformate, ethyl acetoacetate, Dowtherm A, 95–254 °C, 8 h, 52–58% yield; (b) arylalkyl bromide, K2CO3, DMF, 100 °C, 50–75% yield; (c) diethyl oxalate, C2H5ONa, THF, room temp, 10 min, 62–100% yield; (d) 1 N NaOH, THF/CH3OH, room temp, 40 min, 38–100% yield.