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. Author manuscript; available in PMC: 2016 Feb 26.
Published in final edited form as: J Med Chem. 2015 Jul 16;58(15):6033–6047. doi: 10.1021/acs.jmedchem.5b00635

Scheme 1. Synthesis of Substituted 2-(Isoxazol-3-yl)-2-oxo-N′-phenyl-acetohydrazonoyl Cyanide Analogues with Modification on the Phenyl and Isoxazol Ringsa.

Scheme 1

aReagents and conditions: (a) NaH, THF, 0 °C to rt; (b) NH2OH·HCl, EtOH/THF, rt to reflux, 30–87% for two steps; (c) CH3CN, MeLi, THF, −78 °C; (d) 2 N HCl, NaNO2, H2O, 0 °C; (e) 5a–e, NaOAc, EtOH, 24–76% for three steps.