A synthetic method of 3-seleno indoles
A technology of selenoindole and synthesis method, applied in the direction of organic chemistry and the like, can solve the problems of dependence, narrow substrate range, low universality, etc., and achieves the effects of simple and mild reaction conditions, easy operation, and cheap and easily available raw materials
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[0037] Example 1
[0038] Synthesis of 1H-indol-3-yl-(Z)-N,N-diethyl-N'-(3-nitrophenyl)aminocarboximide selenoate
[0039] Weigh 0.3 mmol 3-nitrophenyl isonitrile (the compound corresponding to number (1), 0.0444 g), 0.36 mmol Se (0.0284 g), 0.36 mmol indole (the compound corresponding to number (14), 0.0422 g), 0.36 mmol diethylamine (the compound corresponding to number (28), 0.0263g, 38μL), 0.6mmol cesium carbonate (0.2117g) in a 20mL test tube reaction tube, add 2mL tetrahydrofuran as a solvent, and stir for 12 hours at 40℃; After the completion of the reaction, the reaction solution was subjected to rotary drying, sample loading and column chromatography separation (column chromatography separation conditions: the stationary phase was 300-400 mesh silica gel powder, and the mobile phase was ethyl acetate (A) and petroleum ether (B) , The mobile phase change program (A:B) is 1:8) to obtain 0.0810g reaction product.
[0040] The above reaction products were characterized and the...
Example Embodiment
[0043] Example 2
[0044] Synthesis of 1H-indol-3-yl-(Z)-N,N-diethyl-N'-(3-nitrophenyl)aminocarboximide selenoate
[0045] Weigh 0.3 mmol 3-nitrophenyl isonitrile (the compound corresponding to number (1), 0.0444 g), 0.36 mmol Se (0.0284 g), 0.36 mmol indole (the compound corresponding to number (14), 0.0422 g), 0.36 mmol diethylamine (the compound corresponding to number (28), 0.0263g, 38μL), 0.6mmol cesium carbonate (0.2117g) and 0.06mmol 2,2,6,6-tetramethylpiperidine oxide (0.0094g) in In a 20mL test tube reaction tube, add 2mL of tetrahydrofuran as a solvent, and stir the reaction at 40℃ for 16 hours; after the reaction, the reaction solution is subjected to rotary drying, sample loading and column chromatography separation (column chromatography separation condition: stationary phase is 300 ~400 mesh silica gel powder, the mobile phase is ethyl acetate (A) and petroleum ether (B), and the mobile phase change program (A:B) is 1:8) to obtain 0.1171 g of reaction product.
[0046...
Example Embodiment
[0049] Example 3
[0050] Synthesis of 1H-indol-3-yl-(Z)-N,N-diethyl-N'-(4-nitrophenyl)aminocarboximide selenoate
[0051] Weigh 0.3 mmol 4-nitrophenyl isonitrile (the compound corresponding to number (2), 0.0444 g), 0.36 mmol Se (0.0284 g), 0.36 mmol indole (the compound corresponding to number (14), 0.0422 g), 0.36 mmol diethylamine (the compound corresponding to number (28), 0.0263g, 38μL), 0.6mmol cesium carbonate (0.2117g) and 0.06mmol 2,2,6,6-tetramethylpiperidine oxide (0.0094g) in In a 20mL test tube reaction tube, add 2mL of tetrahydrofuran as a solvent, and stir the reaction at 40℃ for 16 hours; after the reaction, the reaction solution is subjected to rotary drying, sample loading and column chromatography separation (column chromatography separation condition: stationary phase is 300 ~400 mesh silica gel powder, the mobile phase is ethyl acetate (A) and petroleum ether (B), and the mobile phase change program (A:B) is 1:8) to obtain 0.0679g of the reaction product.
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