Method for synthesizing 3-oxo-pyrrol[2,3-b]indole compounds

A technology of oxopyrrole and 3-b, which is applied in the direction of organic chemistry, can solve the problems of many reaction steps, many side reactions, expensive reagents, etc., and achieve the effect of avoiding many reaction steps, simple operation and high reaction yield

Inactive Publication Date: 2014-08-13
KUNMING INST OF BOTANY - CHINESE ACAD OF SCI
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Problems solved by technology

However, the currently reported methods for synthesizing such compounds have the disadvan

Method used

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  • Method for synthesizing 3-oxo-pyrrol[2,3-b]indole compounds
  • Method for synthesizing 3-oxo-pyrrol[2,3-b]indole compounds

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Experimental program
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Embodiment 1

[0020] Synthesis:

[0021] Under the protection of nitrogen, N-benzenesulfonyl tryptamine (90 mg, 0.3 mmol) was dissolved in acetonitrile (6 mL), and then 1,8-diazabicyclo[5.4.0] eleven Carbon-7-ene (137 mg, 0.9 mmol), after stirring at room temperature for 15 minutes, replace the reaction system with oxygen, then add cobalt chloride (4 mg, 0.03 mmol), continue to stir at room temperature for 36 hours, use The reaction was quenched with dilute hydrochloric acid (2N), the aqueous phase was extracted three times with ethyl acetate (15 ml×3), the organic phases were combined, washed successively with water and saturated brine, dried over anhydrous sodium sulfate, concentrated and then column chromatography to obtain 3- Hydroxypyrrole [2,3-b]indole product (86 mg, 91% yield). 1 H-NMR (400MHz, CDCl 3 ): δ7.96–7.79(m,2H), 7.66–7.57(m,1H), 7.53(dd,J=11.4,4.3Hz,2H), 7.22(d,J=7.4Hz,1H), 7.18( t,J=7.7Hz,1H), 6.80(t,J=7.4Hz,1H), 6.64(d,J=7.9Hz,1H), 5.10(s,1H), 4.97(s,1H), 3.53– 3.32(m,1H...

Embodiment 2

[0023] Synthesis:

[0024] Under the protection of nitrogen, N-acetyltryptamine (61 mg, 0.3 mmol) was dissolved in acetonitrile (6 mL), then potassium tert-butoxide (101 mg, 0.9 mmol) was added, and the mixture was stirred at room temperature for 15 minutes Then, add copper chloride (4 mg, 0.03 mmol) and 2,2,6,6-tetramethylpiperidine-1-oxide (140 mg, 0.9 mmol) in sequence, and continue stirring at room temperature for 24 hours. The reaction was quenched with dilute hydrochloric acid (2N), the aqueous phase was extracted three times with ethyl acetate (15 ml×3), the organic phases were combined, washed with water and saturated brine successively, dried over anhydrous sodium sulfate, concentrated and then column chromatography to obtain 3-oxopyrrole[2,3-b]indole product (79 mg, 89% yield). 1 H-NMR (400MHz, CDCl 3 )δ7.32(d,J=7.2Hz,1H), 7.10(td,J=7.9,1.1Hz,1H), 6.75(t,J=7.2Hz,1H), 6.50(d,J=7.9Hz, 1H), 6.06 (s, 1H), 5.04 (s, 1H), 3.73 (td, J = 10.0, 0.8 Hz, 1H), 3.25 (td, J = 11.0, ...

Embodiment 3

[0026] Synthesis:

[0027] Using the method described in Example 2, using 5-methyl-N-acetyl-tryptamine, 2,2,6,6-tetramethylpiperidine-1-oxide and copper chloride as raw materials, the yield Is 96%. 1 H-NMR (400MHz, CDCl 3 )δ7.13(s,1H), 6.92(dd,J=8.0,1.0Hz,1H), 6.43(d,J=8.0Hz,1H), 6.11(s,1H), 4.88(s,1H), 3.77–3.61(m,1H), 3.26(td,J=10.9,6.7Hz,1H), 2.82–2.68(m,1H), 2.52–2.41(m,1H), 2.28(s,3H), 2.03( s,3H),1.69(s,1H),1.49(ddd,J=12.2,6.9,3.5Hz,2H),1.46-1.33(m,5H),1.29-1.18(m,1H),1.08(s, 3H), 1.04(s, 4H), 0.83(s, 3H), 0.75(s, 3H); 13 C-NMR (100MHz, CDCl 3 )δ169.8,148.3,130.3,130.2,127.8,126.1,109.2,96.2,77.8,59.9,59.2,46.8,40.8,40.3,39.9,32.9,32.4,22.2,20.9,20.5,20.4,17.0.

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Abstract

The invention provides a method for synthesizing 3-oxo-pyrrol[2,3-b]indole compounds, which comprises the following step: carrying out cyclization-free radical quenching reaction on tryptamine or tryptophane and derivatives thereof as raw materials under the actions of catalytic amounts of metal oxidizer and free radical trapping agent to generate a series of 3-oxo-pyrrol[2,3-b]indole compounds by a one-step process. The method is simple to operate, has the advantages of cheap and accessible raw materials and reagents, high reaction yield and high reaction regioselectivity and stereoselectivity, overcomes the defects of multiple reaction steps, multiple side reactions, expensive reagents and the like, and is suitable for synthesizing various 3-oxo-pyrrol[2,3-b]indole compounds.

Description

Technical field: [0001] The invention belongs to the field of chemical synthesis methods, and specifically relates to a method for synthesizing 3-oxopyrrole [2,3-b] indole compounds. The method uses tryptamine or tryptophan and its derivatives as raw materials, Under the action of oxidant and free radical trapping agent, a cyclization-free radical quenching reaction occurs, and a series of 3-oxopyrrole [2,3-b]indole compounds are generated in one step. Background technique: [0002] 3-oxopyrrole [2,3-b] indole compounds are a large family of indole alkaloids. Such compounds are not only complex and variable in structure, but also have a wide range of biological activities, for example: from the fungus Gypsea Var. A competitive cholesterol acyltransferase inhibitor gypsetin isolated from incurvata IFO9228; a potent cytotoxic active alkaloid chaetominine isolated from plant endophytes, and a novel five ring isolated from Malaysian plants The skeleton of the indole alkaloid voating...

Claims

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Application Information

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IPC IPC(8): C07D487/04
CPCC07D487/04
Inventor 夏成峰邓旭梁康江
Owner KUNMING INST OF BOTANY - CHINESE ACAD OF SCI
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