A kind of electrochemical synthesis method of 3-alkyl selenyl quinolinone compound
A technology of an alkylselenyl quinolinone and a synthesis method, which is applied in the directions of organic chemistry, electrolysis components, electrolysis process, etc., can solve the problems of increasing the reaction cost, increasing the difficulty of separation and purification of products, etc., reducing recovery steps, and being beneficial to large-scale The effect of high production and reaction selectivity
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Embodiment 1～2
[0058] The following examples 1-2 all react by the following reaction equation, mainly to investigate the yield situation of different substrates reacting under optimal conditions:
[0059]
[0060] The specific operation steps are: in a 25mL three-neck round bottom flask, add quinolinone (3mmol), dialkyldiselenide (1.5mmol), potassium iodide (0.3mmol), DMSO (10mL), 10mm×10mm×3mm foam Aluminum electrodes were used as anodes and glassy carbon rods with a diameter of 6 mm were used as cathodes. The obtained mixed solution was stirred and reacted under a direct current of 15 mA at room temperature, and the reaction process was tracked by thin-layer chromatography, and the reaction time was 12 hours. After the reaction, 10ml of water was added and the product was precipitated, filtered and dried to obtain the pure product.
Embodiment 1
[0062] Compound A, 3-(methylselanyl)quinolin-4(1H)-one, 97%
[0063] 1 H NMR (400MHz, DMSO-d 6 )δ12.07(s,1H),8.08(d,J=8.4Hz,1H),7.90(s,1H),7.65(t,J=8.4Hz,1H),7.57(d,J=7.8Hz, 1H), 7.33(t, J=8.0Hz, 1H), 2.18(s, 3H);
[0064] 13 C NMR (100MHz, DMSO-d 6 )δ175.0, 139.8, 137.6, 131.9, 125.4, 123.8, 123.2, 118.7, 112.3, 4.8;
[0065] Compound B, 95%, 3-(benzylselanyl)quinolin-4(1H)-one, 95%
[0066]
[0067] 1 H NMR (400MHz, DMSO-d 6 )δ12.00(s,1H),8.15(d,J=7.6Hz,1H),7.97(s,1H),7.65(d,J=7.6Hz,1H),7.56(d,J=8.4Hz, 1H), 7.37(d, J=6.8Hz, 1H), 7.23(s, 4H), 7.15(s, 1H), 4.12(s, 2H);
[0068] 13 C NMR (100MHz, DMSO-d 6 )δ175.4, 141.8, 139.9, 139.7, 132.1, 129.2, 128.7, 126.9, 125.7, 124.3, 124.1, 118.8, 109.7, 28.2.
Embodiment 3
[0070] The experimental procedure is according to Example 1. After the filtrate after the final separation of the product in Example 1 is subjected to simple vacuum distillation to remove moisture, the dimethyl sulfoxide solution containing iodine salt is directly circulated to a new reaction. The number of cyclic reactions is the same as the target The product yield is as follows, indicating that iodine salt and dimethyl sulfoxide can be recycled.
[0071] Reaction times 1 Reaction times 2 Reaction times 3 Reaction times 4 Reaction times 5 98％ 96％ 97％ 94％ 92％
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