Substituted carbazole-indole sulfonate derivative, and preparation method therefor and use thereof
A technology of indole sulfonates and derivatives, applied in chemical instruments and methods, instruments, analytical materials, etc., can solve the problems of limited biological use and industrial use, the sensitivity needs to be further improved, and the water solubility is poor. Competitiveness, low overall cost, and low toxicity
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[0030] The preparation method of the substituted carbazole-indolesulfonate derivative comprises the following steps:
[0031] a. Dissolve N-methylcarbazole in anhydrous DMF, then add phosphorus oxychloride, raise the temperature to 125°C, and react for 1h under nitrogen protection to prepare intermediate 1; the phosphorus oxychloride and N-formazol The molar ratio of N-methylcarbazole is 1:1.4-1.8, and the molar ratio of N,N-dimethylformamide to N-methylcarbazole is 2-4:1.
[0032] b, raw material 1 and cyclamate sultone are refluxed in toluene to prepare intermediate 2; the molar ratio of the 1,1,2-trimethylbenzo[e]indole to cyclamate sultone is 1:1.3~1.6.
[0033] c. Refluxing intermediates 1 and 2 in ethanol, adding ammonium acetate for catalysis, and preparing substituted carbazole-indole sulfonate derivatives; the amount of ammonium acetate is twice the equivalent of intermediate 1; The molar ratio of intermediates 1 and 2 is 1:1.1-1.2.
[0034] In the process of synth...
Embodiment 1
[0037] The synthesis of embodiment 1N-methylcarbazole-3-formaldehyde (intermediate 1):
[0038]
[0039] 3.00 g of N-methylcarbazole (16.55 mmol) was dissolved in 12 mL of DMF, then 3 mL of phosphorus oxychloride was added. The temperature of the reaction was raised to 125° C., under the protection of nitrogen, the reaction was carried out for 1 h, and 60 mL of 20% sodium acetate solution was poured into it while hot. The organic phase was extracted three times with ethyl acetate and dried over anhydrous sodium sulfate. Then the solvent was removed under reduced pressure, and the obtained crude product was separated by a 200-300 mesh fine silica gel column, the eluent was petroleum ether / ethyl acetate 2:1, and finally about 2.86 g of a colorless solid was obtained, with a yield of 82%.
[0040] 1 HNMR (DMSO-d 6 ,400MHz): δ10.09(s,1H), 8.70(s,1H), 8.28(d,1H,J=8.0Hz), 8.06(dd,1H,J=8.7,1.7Hz), 7.52(m, 3H), 7.32 (ddd, 1H, J = 7.5, 7.4, 1.0 Hz), 3.98 (s, 1H).
Embodiment 2
[0041] The synthesis of embodiment 2 intermediate 2:
[0042]
[0043] Add 2.09 g of 1,2,2-trimethylbenzo[e]indole (10 mmol), 1.83 g of 1,3-propane sultone (15 mmol, 1.5 eq) and 10 mL of toluene into a 50 mL round bottom flask and stir , After heating to reflux for 18h, the reaction solution was cooled to room temperature. A pink solid was obtained by filtration and washed three times with 10 mL of acetone. The obtained product was further recrystallized from methanol and ether to obtain 2.48 g of solid (yield: 75%).
[0044] 1 HNMR (CD 3 OD, 400MHz): δ8.34(d, 1H, J=8.4Hz), 8.26(dd, 1H, J=8.8Hz, J=4.4Hz), 8.18~8.14(m, 2H), 7.82(t, 1H ,J=8.0Hz), 7.73(d,1H,J=8.0Hz), 4.88(t,2H,J=8.0Hz), 3.37(s,3H), 3.07(t,2H,J=6.4Hz), 2.49-2.42 (m, 2H), 1.86 (s, 6H).
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