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. Author manuscript; available in PMC: 2014 Apr 1.
Published in final edited form as: Bioorg Med Chem. 2013 Feb 1;21(7):1880–1897. doi: 10.1016/j.bmc.2013.01.046

Scheme 4. Generation of N- and O-alkylated substitution pairs 19a–b and 20a–c.a.

Scheme 4

aReagents and conditions: a) (i) benzoyl isothiocyanate, EtOH, 75°C, 5h, (ii) KOH, EtOH:H2O (2:1) 70°C, 2h; b) R2-X, NaHCO3, DMF, RT-70°C, 30min-16h; c) R3-X, base, EtOH or DMF, 70–80°C, 16–24h.