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. Author manuscript; available in PMC: 2018 Mar 10.
Published in final edited form as: ACS Infect Dis. 2017 Feb 8;3(3):225–236. doi: 10.1021/acsinfecdis.6b00202

Scheme 12. Heterocyclic replacements on the eastern half of 1.

Scheme 12

Reagents and conditions: (a) 22a, AcOH, NaBH3CN, CH3OH, rt, 12 hr; (b) 3M aq. HCl, THF, rt, 1 hr, 80 °C, 1 hr; then DDE-OH, (i-Pr)2NEt, CH2Cl2, CH3OH, rt, 12 hr; (c) Boc2O, K2CO3, CH3CN, H2O, rt, 12 hr; (d) H2NNH2H2O, CH3CN, 45 °C, 3 hr; (e) PhCNO, CH3CN, rt, 12 hr; (f) 2-chlorobenzoxazole, (i-Pr)2NEt, CH3CN, 80 °C, 12 hr; (g) 4-chloropyrimidine, (i-Pr)2NEt, CH3CN, µW, 150 °C, 2 hr; (h) 4M HCl in 1,4-dioxane, rt, 6 hr.