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. Author manuscript; available in PMC: 2016 Oct 22.
Published in final edited form as: J Med Chem. 2015 Oct 7;58(20):7991–8010. doi: 10.1021/acs.jmedchem.5b00805

Scheme 1. Synthetic Routes to PPyQs 5a–f (A) and 8f (B)a.

Scheme 1

aReagents and conditions: (a) NaH 60%, bromoethyl alcohol, cyclopropylmethyl bromide, 3-bromopropionitrile, ethyl chloroacetate, cyclopropylcarbonyl chloride, n-propionyl chloride, anhydrous DMF, rt, 3 h, 47–99%; (b) H2, Pd/C 10%, ethyl acetate, 50 °C, 4–14 h, 90–98%; (c) SnCl2/HCl, CH3OH, reflux, 1.5 h, 47–80%; (d) ethyl benzoylacetate or ethyl dimethoxybenzoylacetate, absolute ethanol, reflux 15 h, 37–87%; (e) diphenyl ether, 250 °C, 10–15 min, 30–76%.