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Method for preparing tetracyclic spiroindoline compound

A technology for indolines and compounds, which is applied in the field of preparing tetracyclic spirocyclic indolines, can solve the problems of limited reaction yields in the range of substrates, and achieve the effect of low cost and simple operation

Active Publication Date: 2021-07-13
SOUTH CHINA UNIV OF TECH
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the reaction must protect the indole and require an excess of oxidant to participate in the reaction, which limits the range of substrates and the reaction yield.

Method used

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  • Method for preparing tetracyclic spiroindoline compound
  • Method for preparing tetracyclic spiroindoline compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] A tetracyclic spirocyclic indoline compound, the preparation method is as follows:

[0036] Add 20-40mL of dichloroethane to a 100mL one-necked flask, and then add 10mmol of NaHSO 3 and 10mmol of 15mmol of lithium chloride and 0.2mmol of Rhodamine 6G were reacted under light at room temperature for 24 hours, and the solvent was removed under reduced pressure to obtain a crude product, which was then separated by flash column chromatography to obtain the product 72.6 mg (91%). The structure of the product characterizes the physical constants: 1 H NMR (500MHz, Chloroform-d) δ8.05–7.99(m,2H),7.48–7.39(m,3H),7.15(m,1H),6.62(d,J=8.0Hz,1H),6.55( d,J=9.0Hz,1H),5.52(s,1H),5.02(s,1H),3.91(d,J=10.0Hz,1H),3.74(d,J=10.0Hz,1H),3.47( m,1H),3.37(m,1H),1.66–1.59(m,2H),0.96(t,J=7.5Hz,3H). 13 C NMR (126MHz, Chloroform-d) δ158.9 (d, J=249.1Hz), 157.9, 149.7 (d, J=7.9Hz), 144.5, 136.8, 132.0 (d, J=8.8Hz), 131.2, 129.9 ,128.5,125.2,115.4(d,J=20.4Hz),108.1(d,J=20.7Hz),106.5(d,J=3.1Hz...

Embodiment 2

[0038] A tetracyclic spirocyclic indoline compound, the preparation method is as follows:

[0039] Add 20-40mL of dichloroethane to a 100mL one-necked flask, and then add 10mmol of NaHSO 3 and 10mmol of 15mmol of lithium chloride and 0.2mmol of Rhodamine 6G were reacted under light at room temperature for 24 hours, and the solvent was removed under reduced pressure to obtain a crude product, which was then separated by flash column chromatography to obtain the product 55.1 mg (70%). The structure of the product characterizes the physical constants: 1 H NMR (500MHz, Chloroform-d)δ8.00(m,2H),7.42(m,3H),7.02–6.92(m,2H),6.72(d,J=8.0Hz,1H),5.29(s, 1H), 5.00(s, 1H), 3.85(d, J=9.5Hz, 1H), 3.65(d, J=9.5Hz, 1H), 3.51(dt, J=14.5, 7.5Hz, 1H), 3.41( dt,J=14.0,7.5Hz,1H),2.23(s,3H),1.64(m,2H),0.98(t,J=7.5Hz,3H). 13 C NMR (126MHz, Chloroform-d) δ162.7, 144.6, 143.5, 137.5, 131.0, 130.8, 129.8, 129.7, 128.5, 125.3, 122.1, 110.6, 84.1, 58.2, 54.4, 45.6, 20.9, 20.7, 11.5.

Embodiment 3

[0041] A tetracyclic spirocyclic indoline compound, the preparation method is as follows:

[0042]Add 20-40mL of dichloroethane to a 100mL one-necked flask, and then add 10mmol of NaHSO 3 and 10mmol of 15mmol of lithium chloride and 0.2mmol of Rhodamine 6G were reacted under light at room temperature for 24 hours, and the solvent was removed under reduced pressure to obtain a crude product, which was then separated by flash column chromatography to obtain the product 66.4 mg (80%). The structure of the product characterizes the physical constants: 1 H NMR (500MHz, Chloroform-d) δ8.03–7.97(m,2H),7.50–7.41(m,3H),7.16(m,1H),7.12(d,J=2.0Hz,1H),6.74( d,J=8.5Hz,1H),5.43(s,1H),5.02(s,1H),3.86(d,J=9.5Hz,1H),3.66(d,J=9.5Hz,1H),3.58– 3.37(m,2H),1.64(m,3H),0.99(t,J=7.5Hz,3H). 13 C NMR (126MHz, Chloroform-d) δ162.3, 145.4, 144.2, 136.7, 131.2, 131.1, 130.3, 129.7, 128.6, 125.9, 125.1, 122.0, 111.6, 83.9, 58.0, 54.2, 45.6, 20.7, 11.4.

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Abstract

The invention discloses a method for preparing a tetracyclic spiroindoline compound. The method comprises the following steps: adding [SO2], indole alkyne amide, an additive and a photocatalyst into an organic solvent, and conducting reacting under illumination to obtain the tetracyclic spiroindoline compound (with a structural formula as shown in the specification), wherein a molar ratio of [SO2] to indole alkyne amide is 10: 1 to 1: 10; a molar ratio of the [SO2] to the additive is 100: 1 to 1: 10; a molar ratio of the [SO2] to the photocatalyst is 500: 1 to 10: 1; and [SO2] is DABCO.SO2, sodium pyrosulfite, sodium hydrosulfite or sodium hydrogen sulfite. According to the preparation method, cheap inorganic salt is used as a sulfonylation reagent, transition metal catalysis is not needed, strict anhydrous conditions and low-temperature and high-temperature operation are not needed, dangerous peroxides are not needed, expensive photocatalysts are not needed, operation is simple, and cost is low.

Description

technical field [0001] The invention belongs to the field of synthesis of indoline compounds, in particular to a method for preparing tetracyclic spiro indoline compounds. Background technique [0002] As a typical representative of nitrogen heterocycles, indole rings widely exist in natural products, especially some alkaloid compounds, which have always attracted the attention of the organic synthesis community because of their inherent biological activities. Among them, the polycyclic indoline skeleton is particularly attractive as the basic skeleton structure of complex natural products, such as (-)-perophoramidine, (-)-aspidospermidine, (-)-kopsinine and malagashanine, all of which have polycyclic indoline moiety. Due to the existence of multiple rings, such three-dimensional structure molecules have strong tension, and their synthesis has always been a huge challenge. To date, many chemists have devoted themselves to synthesizing these advantageous molecules through d...

Claims

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Application Information

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IPC IPC(8): C07D495/20
CPCC07D495/20
Inventor 尹标林罗家骏
Owner SOUTH CHINA UNIV OF TECH
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