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. Author manuscript; available in PMC: 2015 Mar 13.
Published in final edited form as: J Med Chem. 2013 Nov 6;57(5):1914–1931. doi: 10.1021/jm401329s

Scheme 4. Synthesis of 2,5,7,8-tetrasubstituted quinoline core.

Scheme 4

Reagents and conditions: (a) 4-nitrobenzaldehyde, N-vinylpyrrolidin-2-one, BiCl3, CH3CN; (b) CAN, CH3CN, 0 °C, 22% two steps; (c) Fe, NH4Cl, MeOH, water, reflux, 73%; (d) MsCl, pyridine, CH2Cl2, 0 °C, 86%.