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. 2020 Feb 24;11(3):392–410. doi: 10.1039/c9md00594c

Scheme 1. Synthesis of HCT compounds 1–15 from simple isoquinolines. (a) Allyl chloroformate, MeMgBr, THF; (b) Pd(PPh3)4, morpholine; DDQ, CH2Cl2; (c) SeO2, 1,4-dioxane, 60 °C; (d) appropriate thiosemicarbazide, HCl, EtOH, reflux or microwave 50 °C; (e) KNO3, H2SO4; (f) Fe, HCl, MeOH, reflux; (g) Boc2O, DMAP, TEA, THF; (h) Boc2O, DMAP, TEA, THF; NaHCO3, MeOH, reflux or K2CO3, MeOH, reflux; (i) NaH, THF; MeI. HCTs 13, 68, and 1113 synthesized through route A; HCTs 5 and 10 synthesized through route B; HCTs 4, 9, 14, and 15 synthesized through route C. See Experimental section for full synthetic details.

Scheme 1