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Preparation method of natural product 2-methyl-3-methoxy-carbazole-1,4-benzoquinone

A technology of methoxy and methyl, which is applied in the field of preparation of natural product 2-methyl-3-methoxy-carbazole-1,4-benzoquinone, can solve the problems of low total yield, high cost, and carbazole The preparation process of oxazolone is complicated, and the preparation method is simple, the selectivity is good, and the separation is convenient.

Inactive Publication Date: 2014-05-21
NORTHWEST UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The preparation process of disubstituted benzoquinones is complicated, and noble metal catalysts are used in the synthesis process, and the cost is high
The preparation process of carbazolone is complex and the overall yield is low
[0007] The above several synthesis strategies for 2-methyl-3-methoxy-carbazole-1,4-benzoquinone are complicated to operate, and the preparation process of raw materials is relatively cumbersome.

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] Under the protection of argon, add 3-bromo-N-Ts indole (186mg, 0.53mmol) into the reaction bottle and dissolve it in 5mL of anhydrous tetrahydrofuran. After the system is cooled to -110°C, slowly add n-butyllithium (2.4M n-hexane solution, 0.22mL, 0.53mmol), stirred for 5 minutes. Then slowly add 3-methoxy-4-methyl-3-cyclobutene-1,2-dione tetrahydrofuran solution (55 mg (0.44 mmol) 3-methoxy-4-methanol Base-3-cyclobutene-1,2-dione was prepared by dissolving in 1mL THF), after stirring for 10 minutes, the reaction was quenched with saturated sodium bicarbonate solution, extracted with ethyl acetate, Na 2 SO 4 After drying and concentrating, it was dissolved in 5 mL of N,N'-dimethylformamide (DMF), heated to reflux for 3 hours, concentrated and then separated by chromatographic column (eluent: ethyl acetate:petroleum ether=1:8 ) to obtain the natural product 2-methyl-3-methoxy-carbazole-1,4-benzoquinone (74.7mg, 66%). IR(neat): 3259, 2952, 1641, 1531, 1153, 741cm -1 ....

Embodiment 2

[0022] Under the protection of argon, add 3-bromo-N-Ts indole (186mg, 0.53mmol) into the reaction bottle and dissolve it with 5mL of anhydrous ether. After the system is cooled to -110°C, slowly add n-butyllithium (2.4M n-hexane solution, 0.22mL, 0.53mmol), stirred for 5 minutes. Then slowly add 3-methoxy-4-methyl-3-cyclobutene-1,2-dione ether solution (55 mg (0.44 mmol) 3-methoxy-4-methyl base-3-cyclobutene-1,2-dione was prepared by dissolving in 1mL ether), after stirring for 10 minutes, the reaction was quenched with saturated sodium bicarbonate solution, extracted with ethyl acetate, Na 2 SO 4 After drying and concentrating, it was dissolved in 5 mL of N,N'-dimethylformamide (DMF), heated to reflux for 3 hours, concentrated and then separated by chromatographic column (eluent: ethyl acetate:petroleum ether=1:8 ) to obtain the natural product 2-methyl-3-methoxy-carbazole-1,4-benzoquinone (67.9mg, 60%).

Embodiment 3

[0024] Under the protection of argon, add 3-bromo-N-Ts indole (186mg, 0.53mmol) into the reaction bottle and dissolve it with 5mL of anhydrous dioxane. After the system is cooled to -110°C, tert-butyllithium (1.3M Pentane solution, 0.41mL, 0.53mmol), stirred for 5 minutes. Then slowly add 3-methoxy-4-methyl-3-cyclobutene-1,2-dione dioxane solution (55 mg (0.44 mmol) 3-methoxy-4 -Methyl-3-cyclobutene-1,2-dione was prepared by dissolving in 1mL of dioxane), after stirring for 10 minutes, the reaction was quenched with saturated sodium bicarbonate solution, extracted with ethyl acetate, Na 2 SO 4 After drying and concentrating, it was dissolved in 5 mL of dimethyl sulfoxide (DMSO), heated to reflux for 3 hours, concentrated and separated by chromatographic column (eluent: ethyl acetate:petroleum ether=1:8) to obtain the natural product 2 - Methyl-3-methoxy-carbazole-1,4-benzoquinone (70.2 mg, 62%).

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Abstract

The invention discloses a preparation method of 2-methyl-3-methoxy-carbazole-1,4-benzoquinone. In the preparation method, 3-bromo-N-Ts indole reacts with 3-methoxy-4-methyl-3-cyclobutene-1,2-diketone to obtain 2-methyl-3-methoxy-carbazole-1,4-benzoquinone, wherein Ts is p-toluenesulfonyl. In the invention, a natural product 2-methyl-3-methoxy-carbazole-1,4-benzoquinone is synthesized by use of commercially available raw materials; the preparation method is simple and realizes convenient separation, high yield and good selectivity.

Description

technical field [0001] The invention relates to a preparation method of a natural product 2-methyl-3-methoxy-carbazole-1,4-benzoquinone, which belongs to the technical field of chemical synthesis. Background technique [0002] 2-Methyl-3-methoxy-carbazole-1,4-benzoquinone is a natural product extracted from Streptomyces CMU-JT005 by Lumyong's research group. Biological experiments show that 2-methyl-3-methoxy-carbazole-1,4-benzoquinone has anti-tuberculosis activity. Since the content of this natural product in the strain is low, it is difficult to separate, so it is extracted and isolated from the strain alone. The cost is too high, which largely limits its further research in vivo and clinically. Therefore, it is of great significance to realize the concise and efficient synthesis of this natural product. [0003] 2-Methyl-3-methoxy-carbazole-1,4-benzoquinone is also an important synthetic intermediate of various carbazole alkaloids. Hans-Joachim Kniilker's research gro...

Claims

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Application Information

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IPC IPC(8): C07D209/88
CPCC07D209/88
Inventor 胡向东张九岭安勇
Owner NORTHWEST UNIV
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