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. 2023 Jun 24;34(7):1271–1281. doi: 10.1021/acs.bioconjchem.3c00163

Figure 2.

Figure 2

General procedures for synthesis of a library of CBXs. Reaction conditions: (a) corresponding ortho-substituted aniline (−NH2, −NHMe, −OH, and −SH), Appel’s salt (4,5-dichloro-1,2,3-dithiazolium chloride), pyridine, 70 °C, 16 h; (b) MeI, K2CO3, MeCN, rt, 72 h; (c) 1. corresponding 2-bromoaniline, Appel’s salt (4,5-dichloro-1,2,3-dithiazolium chloride), pyridine, dry DCM, rt, 2 h; 2. CuI, dry pyridine, MWI, 115 °C, 20 min; (d) NaCN, DABCO, MeCN/H2O, rt, 7–24 h (for 83: KCN, DABCO, dry DMF, 100 °C, 48 h); (e) Al, I2, dry MeCN, 80 °C, 18 h; (f) AlCl3, dry DCM, 40 °C, 18 h (for 41: Al, I2, dry MeCN, 80 °C, 18 h); (g) Fe, AcOH, rt, 2 h.