3-aryl-3'-aminobiquaternary carbon bisoxindole compound and its synthesis method and application

A technology of indole compound and synthesis method, which is applied in the field of 3-aryl-3'-aminobiquaternary carbon bisoxindole compound and its synthesis, and can solve unfavorable 3-aryl-3'-aminobiquaternary carbon Problems such as application of bisoxindole building block, low total reaction yield, and long process time are achieved to achieve high atom economy, good application prospects, and high diastereoselectivity.

Active Publication Date: 2022-01-07
EAST CHINA NORMAL UNIV
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Problems solved by technology

[0004] Carry out synthesis for 3-aryl-3'-aminobiquaternary carbon bisoxindole building block according to existing method, all exist synthetic route is longer, and step is loaded down with trivial details (more than 5 steps), and total reaction yield is lower (<30 %), there are more waste materials produced, and the defects such as process time-consuming are longer, are unfavorable for the application of 3-aryl-3'-aminobiquaternary carbon bisoxindole building blocks in drug synthesis

Method used

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  • 3-aryl-3'-aminobiquaternary carbon bisoxindole compound and its synthesis method and application
  • 3-aryl-3'-aminobiquaternary carbon bisoxindole compound and its synthesis method and application
  • 3-aryl-3'-aminobiquaternary carbon bisoxindole compound and its synthesis method and application

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Experimental program
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Embodiment 1

[0068]

[0069] N-Benzyl-N'-Boc isatinimine (0.3mmol), N, N-dibenzylaniline (0.33mmol), Rh 2 (OAc) 4 (0.05mmol) and Molecular sieves (0.2 g) were dissolved in dichloromethane (1.5 mL), and then N-benzyl isatin diazo (0.33 mmol) dissolved in dichloromethane (1 ml) was added to the reaction system within one hour using a peristaltic pump , the reaction was carried out at room temperature, and after the dropwise addition was completed, it was stirred for two hours. Its structure is shown in Formula 4a. The crude product was subjected to column chromatography (ethyl acetate: petroleum ether = 1:20-1:5) to obtain a pure product with a yield of 80%. nuclear magnetic resonance 1 H NMR, 13 C NMR spectrum as figure 1 as shown, 1 H NMR (400MHz, CDCl 3 )δ8.17 (s,1H),7.50(d,J=8.9Hz,2H),7.36–7.30(m,6H),7.29–7.17(m,10H),7.14–7.06(m,3H), 7.05 –6.99(m,1H),6.89(d,J=6.9Hz,2H),6.80(t,J=7.5Hz,1H),6.69(d,J=9.2Hz,2H),6.63 –6.49(m, 3H), 6.36(d, J=7.3Hz, 1H), 5.86(s, 1H), 5.05(d, J=16.0H...

Embodiment 2

[0071]

[0072] N-methyl-N'-Boc isatinimine (0.3mmol), N,N-dibenzylaniline (0.33mmol), Rh 2 (OAc) 4 (0.05mmol) and Molecular sieves (0.2 g) were dissolved in dichloromethane (1.5 mL), and then N-benzyl isatin diazo (0.33 mmol) dissolved in dichloromethane (1 ml) was added to the reaction system within one hour using a peristaltic pump , the reaction was carried out at room temperature, and after the dropwise addition was completed, it was stirred for two hours. Its structure is shown in formula 4b. The crude product was subjected to column chromatography (ethyl acetate:petroleum ether=1:20~1:5) to obtain a pure product with a yield of 66%. 1 H NMR (400MHz, CDCl 3 )δ8.12(s,1H),7.48(d,J=8.9Hz,2H),7.33(q,J=6.4,6.0Hz,5H),7.30–7.21(m,11H),7.09–7.02(m ,1H),6.82(t,J=7.5Hz,1H),6.74–6.65(m,4H), 6.59(d,J=7.8Hz,1H),6.29(d,J=6.8Hz,1H),5.99 (s,1H),5.02(d,J=16.1Hz,1H),4.91(d,J=16.0Hz,1H),4.76–4.60(m,4H),2.73(s,3H),1.23(s, 9H). 13 C NMR (101MHz, CDCl 3)δ174.71, 148.74,145.11,143....

Embodiment 3

[0074]

[0075] N-methyl-N'-Boc isatinimine (0.3mmol), N,N-dibenzylaniline (0.33mmol), Rh 2 (OAc) 4 (0.05mmol) and Molecular sieves (0.2 g) were dissolved in dichloromethane (1.5 mL), and then N-benzyl isatin diazo (0.33 mmol) dissolved in dichloromethane (1 ml) was added to the reaction system within one hour using a peristaltic pump , the reaction was carried out at room temperature, and after the dropwise addition was completed, it was stirred for two hours. Its structure is shown in Formula 4c. The crude product was subjected to column chromatography (ethyl acetate: petroleum ether = 1:20-1:5) to obtain a pure product with a yield of 60%. 1 H NMR (400MHz, CDCl 3 )δ7.97(s,1H),7.55(d,J=7.5Hz,2H),7.37–7.19(m,16H),7.07(t,J=7.7Hz,1H),6.85(d,J=8.1 Hz,1H),6.74(t,J=7.6Hz,1H),6.67–6.57(m,4H), 6.39(d,J=7.5Hz,1H),5.03(d,J=16.0Hz,1H), 4.90(d,J=16.0Hz,1H),4.74–4.57(m,4H), 2.64(s,3H),1.32(s,9H). 13 C NMR (101MHz, CDCl 3 )δ174.19,148.90,146.82,142.86,138.29, 135.45,131.12,130....

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Abstract

The invention discloses a synthesis method and application of a 3-aryl-3'-aminobiquaternary carbobisoxindole compound, which uses diazo compounds, N,N-disubstituted anilines, and isatinimine compounds as raw materials. Using rhodium acetate as a catalyst, an organic solvent as a solvent, and molecular sieves as an additive, the biquaternary carbon bisoxindole compound is obtained through one-step reaction at room temperature. The synthesis method of the biquaternary carbon bisoxindole compound of the present invention has the advantages of efficient atom economy, high selectivity, low catalyst consumption, simple and safe operation, etc. The synthesized biquaternary carbon bisoxindole compound can be used as an important medicine and Chemical intermediates have broad application prospects in the pharmaceutical field.

Description

technical field [0001] The invention belongs to the fields of synthetic medicine and chemical industry, and mainly relates to a 3-aryl-3'-aminobiquaternary carbon bisoxindole compound and its synthesis method and application. Background technique [0002] Oxindole is a heterocyclic structure that widely exists in nature, and many natural products with biological activity contain this structure. Moreover, such compounds usually have certain physiological and biological activities, so they have attracted extensive attention in the field of medicinal chemistry, and are considered to be a class of organic small molecule core structures with great potential pharmaceutical value. [0003] However, the synthesis of 3,3'-disubstituted bisoxindoles has always been a difficult point in organic synthesis. From the perspective of traditional organic synthesis methods, this type of skeleton exists: the structure is crowded, the steric hindrance of the compound is large, it contains two ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D209/34A61P35/00A61P25/24
Inventor 刘顺英牛荔纪佳丽车久威皮柔董素珍胡文浩
Owner EAST CHINA NORMAL UNIV
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