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. 2016 Mar 21;21(3):390. doi: 10.3390/molecules21030390

Scheme 1.

Synthetic route and chemical structures of compounds 46 and 7a7x. Reagents and conditions: (a) i: benzaldehyde, methanol, r.t.; ii: NaBH4, r.t., 98%; (b) α-ketoglutaric acid, p-TSA, dry toluene: dioxane = 3:2, DST, reflux, 83%; (c) HCOONH4, 5% Pd/C, methanol: toluene = 1:1, reflux, 75%; (d) 5% Pd/C, xylene, reflux, 90%; (e) BBr3, dry DCM, −78 °C to r.t., 63%; (f) acyl chloride, TEA, dry DCM, 0 °C, 48%–86%.

Scheme 1

7a: R = C6H5 7g: R = 3′-ClC6H4 7m: R = 4′-FC6H4 7s: R = CH3
7b: R = 2′-pyridyl 7h: R = 4′-ClC6H4 7n: R = 2′-CF3C6H4 7t: R = CH3CH2
7c: R = 2′-CH3C6H4 7i: R = 2′,4′-Cl2C6H3 70: R = 3′-CF3C6H4 7u: R = CH3(CH2)2
7d: R = 3′-CH3C6H4 7j: R = 4′-CH3OC6H4 7p: R = 4′-CF3C6H4 7v: R = CH3(CH2)3
7e: R = 4′-CH3C6H4 7k: R = 2′-FC6H4 7q: R = 1′-naphthyl 7w: R = CH3(CH2)4
7f: R = 2′-ClC6H4 7l: R = 3′-FC6H4 7r: R = 2′-naphthyl 7x: R = CH3(CH2)10