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. 2020 Mar 5;11(5):798–805. doi: 10.1021/acsmedchemlett.9b00617

Scheme 3. Synthetic Route to 10ai and 11ai Derivatives.

Scheme 3

Reagents and conditions: (i) acetone, NaOH 1 N, 80 °C, 5 h, 41–63% yield; (ii) TosMIC, NaH, 2:1 Et2O dry/DMSO dry, N2, room temp, 1 h, 87–100% yield; (iii) proper arylalkyl halide, DMF, K2CO3, 80 °C, 2–24 h, 15–59% yield; (iv) diethyl oxalate, EtONa, THF dry, N2, room temp, 2 h, 55–100% yield; (v) MeOH, NH2NH2 dihydrochloride, Et3N, CH3COOH gl, room temp, 2 h, 20–65% yield; (vi) THF, NaOH 20%, 90 °C, 12 h, 62–100% yield.