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Synthesis of compounds 2–5.
Reagents and conditions: (a) (i) phthalic anhydride, NaOH, H2O, 16 h, rt; (ii) pyridine, DMAP, Ac2O, 16 h, rt; (b) TMSN3, FeCl3 as catalyst, DCM, rt; (c) Pd/C, MeOH, H2, 2 h, rt; (d) TBTU, DIPEA. DMF 3 h, rt; (e) ethylenediamine/butanol (1:1), 90 °C, 2 h; (f) Jones reagent, acetone, 0 °C, 20 min; (g) NaH, DMF, 80 °C; (h) CuI, acetic acid, DIPEA.
