3-aryl-3'-amino bis(quaternary carbon) bis(oxindole) compounds and synthetic method and applications thereof

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 The application of bisoxindole building blocks, low total reaction yield, long synthetic route and other problems achieve the effect of less reaction steps, high atom economy and less waste

Active Publication Date: 2019-05-21
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 react...

Method used

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  • 3-aryl-3'-amino bis(quaternary carbon) bis(oxindole) compounds and synthetic method and applications thereof
  • 3-aryl-3'-amino bis(quaternary carbon) bis(oxindole) compounds and synthetic method and applications thereof
  • 3-aryl-3'-amino bis(quaternary carbon) bis(oxindole) compounds and synthetic method and applications thereof

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Experimental program
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Effect test

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=16.0Hz, ...

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)δ174.71,148.74,145.11,143.10...

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...

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Abstract

3-aryl-3'-amino bis(quaternary carbon) bis(oxindole) compounds and a synthetic method and applications thereof are disclosed. The compounds are prepared from diazo compounds, N,N-disubstituted anilineand isatin imine compound by adopting rhodium acetate as a catalyst, an organic solvent as a solvent and a 4A molecular sieve as an additive through one-step reaction at room temperature. The methodhas advantages of efficient atom economy, high selectivity, a low dosage of the catalyst, simple and safe operation, and the like. The synthesized bis(quaternary carbon) bis(oxindole) compounds can beadopted as important medical and chemical intermediates and have wide application prospects in the medicinal 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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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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