Simple, convenient and efficient preparation method of abrotanum sulphone-aminodithioformic acid ester type compound
A technology for aminodithiocarboxylate and ester compounds, which is applied in the synthesis field of preparing artemisinone-aminodithiocarboxylate compounds, can solve the problems of poor oil solubility and water solubility, high clinical recurrence rate, and heat insufficiency. Stability and other issues, to achieve the effect of reducing energy consumption, high substrate conversion rate, and mild reaction conditions
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Embodiment 1
[0016] Embodiment 1: artesunate sulfone iodide and N -Methylpiperazine prepares carbamate, and reaction equation is as follows:
[0017]
[0018] At room temperature, add 0.25 mmol N —Methylpiperazine, 1 mL carbon disulfide, 1 mL anhydrous chloroform and 0.25 mmol triethylamine, after stirring for 3 minutes, add 0.5 mmol artemisinic sulfone iodide, heat up to reflux, react for 3 h, track with TLC, use acetic acid Extracted with ethyl ester, combined extracts, dried with anhydrous magnesium sulfate, distilled off the solvent and purified by silica gel column chromatography [eluent: V (dichloromethane): V (methanol) = 15:1] to obtain a yellow liquid, Yield 60%; [ a ] +140 (c0.50, CH 2 Cl 2 ); 1 H NMR (400 MHz, CDCl 3 ) δ: 5.29 (s, J = 5.1 Hz, 1H), 4.36 (s,2H), 4.18 (d, J = 10.2 Hz, 1H), 3.97 (s, 2H), 3.48 (d, J = 12.7 Hz, 1H), 3.42– 3.34 (m, 2H), 3.34 – 3.26 (t, 4H), 3.11 – 2.96 (t, 1H), 2.87 (d, J = 13.4Hz, 1H), 2.60 – 2.46 (m, 5H), 2.39 – 2.31 (m, 4H), 2.07...
Embodiment 2
[0019] Embodiment 2: artesunate sulfone iodide and N -Ethylpiperazine prepares carbamate, and reaction equation is as follows:
[0020]
[0021] At room temperature, add 0.25 mmol N —Ethylpiperazine, 1 mL carbon disulfide, 1 mL anhydrous chloroform and 0.25 mmol triethylamine, after stirring for 3 minutes, add 0.5 mmol artemisinic sulfone iodide, heat up to reflux, react for 3 h, track with TLC, use acetic acid Extract with ethyl ester, combine the extracts, dry with anhydrous magnesium sulfate, spin off the solvent and purify by silica gel column chromatography [eluent: V (dichloromethane): V (methanol) = 15:1] to obtain a yellow liquid, Yield 55%; [ a ] +100 (c0.50, CH 2 Cl 2 ); 1 H NMR (400 MHz, CDCl 3 ) δ: 5.27 (s, J = 5.1 Hz, 1H), 4.35 (s,2H), 4.16 (d, J = 10.2 Hz, 1H), 3.95 (s, 2H), 3.71 – 3.57 (m, 1H), 3.46 (d, J = 7.0 Hz, 1H), 3.38 – 3.24 (m, 5H), 3.10 – 2.99 (t, 1H), 2.85 (d, J = 13.4Hz, 1H), 2.67 – 2.39 (m, 7H), 2.39 – 2.27 (t, 1H), 2.03 – 1.95 (m,...
Embodiment 3
[0022] Embodiment 3: artesunate sulfone iodide and N - pyridylpiperazine prepares carbamate, reaction equation is as follows:
[0023]
[0024] At room temperature, add 0.25 mmol N —Pyridylpiperazine, 1 mL carbon disulfide, 1 mL anhydrous chloroform and 0.25 mmol triethylamine, after stirring for 3 minutes, add 0.5 mmol artesunone iodide, heat up to reflux, react for 3 h, trace with TLC, use acetic acid Extract with ethyl ester, combine the extracts, dry with anhydrous magnesium sulfate, spin off the solvent and purify by silica gel column chromatography [eluent: V (dichloromethane): V (methanol) = 15:1] to obtain a yellow liquid, Yield 56.5%; [ a ] +233(c 0.50, CH 2 Cl 2 ); 1 H NMR (400 MHz, CDCl 3 ) δ: 8.19 (dd, J = 4.8, 1.3 Hz, 1H),7.51 (m, J = 8.8, 6.5, 1.9 Hz, 1H), 6.72 – 6.57 (m, 2H), 5.28 (s, J = 5.0 Hz,1H), 4.44 (m, J = 16.7, 7.5 Hz, 2H), 4.16 (d, J = 10.2 Hz, 1H), 3.82 – 3.57(m, 5H), 3.42 – 3.20 (m, 4H), 3.11 – 2.95 (m, 1H), 2.86 (d, J = 13.4 Hz,...
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