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Polysubstituted indole compound and preparation method thereof

A technology for indoles and compounds, which is applied in the field of polysubstituted indoles and their preparation, can solve the problems of harsh reaction conditions, difficult to meet industrial production requirements, difficult to obtain reaction raw materials, etc., and achieves the effect of easy operation

Active Publication Date: 2015-02-11
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0011] But above-mentioned method has respective limitation, and the reaction condition of most synthetic methods is harsher; Or reaction raw material is difficult to obtain, is difficult to meet industrial production requirement; Or it is difficult to synthesize polyfunctional group substituted indole compound

Method used

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  • Polysubstituted indole compound and preparation method thereof
  • Polysubstituted indole compound and preparation method thereof
  • Polysubstituted indole compound and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0047] A multi-substituted indole compound, the preparation method is as follows:

[0048] (1) Add 70mL of absolute ethanol to a 250mL single-necked flask, and then add 10mmol of And 10mmol of p-toluenesulfonyl hydrazide, reflux reaction at 70°C for 12 hours to carry out dehydration condensation, recrystallization after cooling to room temperature to obtain

[0049] Among them, the R in 2 for hydrogen, R 4 is phenyl;

[0050] (2) Under nitrogen protection, add 5mmol of step (1) gained in 100mL three-necked flask , 0.25 mmol of Pd 2 (dba) 3 , 0.5mmol of dppf, 20mmol of potassium carbonate, 25mL of tetrahydrofuran and 10mmol of After stirring and reacting at 90°C for 6 hours, cool to room temperature, remove the solvent, and separate by column chromatography to obtain the multi-substituted indole compound, whose structural formula is Yield 76%;

[0051] Among them, the Middle R 1 for hydrogen, R 3 Ethyl (-CH 2 -CH 3 ).

[0052] For the polysubstituted indo...

Embodiment 2

[0057] Add 60mL of absolute ethanol to a 250mL single-necked flask, and then add 10mmol of And 10mmol of p-toluenesulfonyl hydrazide, reflux reaction at 70°C for 12 hours to carry out dehydration condensation, recrystallization after cooling to room temperature to obtain

[0058] (2) Under nitrogen protection, add 5mmol of step (1) gained in 100mL three-necked flask 0.25 mmol of Pd 2 (dba) 3 , 0.5mmol of dppf, 20mmol of potassium carbonate, 25mL of tetrahydrofuran and 10mmol of After stirring and reacting at 90°C for 6 hours, cool to room temperature, remove the solvent, and separate by column chromatography to obtain the multi-substituted indole compound, whose structural formula is

[0059] Among them, the Middle R 1 for hydrogen, R 3 Ethyl (-CH 2 -CH 3 ).

[0060] For the polysubstituted indole compounds Carry out measurement analysis, its physical constant is:

[0061] 1 H NMR (400MHz, CDCl 3 )δ9.54 (d, J = 7.6Hz, 1H), 7.62 (d, J = 8.1Hz, 1H), 7.57 (d...

Embodiment 3

[0065] (1) Add 80mL of absolute ethanol to a 250mL single-necked flask, and then add 10mmol of And 10mmol of p-toluenesulfonylhydrazide, reflux reaction at 70°C for 24 hours to carry out dehydration condensation, recrystallization after cooling to room temperature to obtain

[0066] (2) Under nitrogen protection, add 5mmol of step (1) gained in 100mL three-necked flask 0.25 mmol of Pd 2 (dba) 3 , 0.5mmol of dppf, 20mmol of potassium carbonate, 20mL of tetrahydrofuran and 10mmol of After stirring and reacting at 90°C for 10 hours, cool to room temperature, remove the solvent, and separate by column chromatography to obtain the polysubstituted indole compound, whose structural formula is

[0067] Among them, the Middle R 1 for hydrogen, R 3 Ethyl (-CH 2 -CH 3 ).

[0068] For the polysubstituted indole compounds Carry out measurement analysis, its physical constant is:

[0069] 1 H NMR (400MHz, CDCl 3 )δ9.55(d, J=7.6Hz, 1H), 7.60(t, J=12.6Hz, 2H), 7.37(q, J=...

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Abstract

The invention belongs to the field of fine chemistry raw materials, and in particular relates to a polysubstituted indole compound and a preparation method thereof. The polysubstituted indole compound has a structural formula as shown in the specification. The preparation method of the polysubstituted indoles compound comprises the following steps: firstly adding a compound I as shown in the specificaiotion and p-toluenesulfonhydrazide in an organic solvent, refluxing to obtain a compound II as shown in the specification, and then adding a compound III as shown in the specification in the solvent, stirring and reacting to obtain the polysubstituted indole compound as shown in the specification under the effect of transition metal catalyst, ligand and alkali.

Description

technical field [0001] The invention belongs to the field of fine chemical raw materials, and in particular relates to a multi-substituted indole compound and a preparation method thereof. Background technique [0002] Indole is an important fine chemical raw material, and its application and synthesis methods have been continuously studied. Substituted indole compounds are mainly used as raw materials for pesticides, medicines, spices and dyes. [0003] In terms of agricultural plant growth regulators and fungicides, indole derivatives such as indole acetic acid and indole-3-butyric acid are important broad-spectrum plant growth regulators. They are excellent for promoting rooting of herbaceous and woody ornamental cuttings. [0004] In the pharmaceutical industry, indole compounds have particularly important uses because of their unique structures. On the one hand, many natural substances with strong physiological activity contain indole ring structures. For example, t...

Claims

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Application Information

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IPC IPC(8): C07D209/12C07D409/04
CPCC07D209/12C07D409/04
Inventor 尹标林张晓瑜
Owner SOUTH CHINA UNIV OF TECH
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