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Method for synthesizing substituted cyclopropane compounds through dearomatizing indole

A compound and aromatization technology, applied in organic chemistry and other directions, can solve the problems of poor chemical selectivity and stereoselectivity of products, expensive reagents or catalysts, etc., and achieve the effects of complete conversion of raw materials, convenient separation and high yield.

Inactive Publication Date: 2015-07-29
DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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  • Claims
  • Application Information

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Problems solved by technology

[0003] Due to the severe reaction conditions used in most indole dearomatization and synthesis of cyclopropane compounds, the reaction reagents or catalysts are expensive, and the resulting products have poor chemoselectivity and stereoselectivity, which prevents the widespread application of these methods.

Method used

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  • Method for synthesizing substituted cyclopropane compounds through dearomatizing indole
  • Method for synthesizing substituted cyclopropane compounds through dearomatizing indole
  • Method for synthesizing substituted cyclopropane compounds through dearomatizing indole

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Experimental program
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Effect test

Embodiment 1

[0029] Embodiment 1: condition optimization

[0030]

[0031] In a nitrogen-protected reaction flask, add substituted indole 1a (0.25 mmol), sulfur ylide 2a (0.38 mmol), potassium carbonate (0.75 mmol), and then add 3 ml of dry isopropanol and 0.3 ml of ethanol. After reacting at room temperature for 12 h, 3 mL of water was added to quench the reaction. After standing still for liquid separation, the aqueous layer was extracted three times with dichloromethane (3×15 mL). After combining the organic layers, they were dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure, and the product was obtained by silica gel column chromatography, and the reaction structure was as follows:

[0032]

[0033] Using the same conditions as above, except that different solvents and bases were used, the yield of the product is shown in Table 1.

[0034] Table 1. Optimization of conditions for the synthesis of cyclopropane compounds by dearomatization of indo...

Embodiment 2

[0036] Example 2: Dearomatization of substituted indoles to synthesize cyclopropane compound 3

[0037] In a nitrogen-protected reaction flask, add substituted indole 1a (0.25 mmol), sulfur ylide 2a (0.38 mmol), potassium carbonate (0.75 mmol), and then add 3 ml of dry isopropanol and 0.3 ml of ethanol. After reacting at room temperature for 12 h, 3 mL of water was added to quench the reaction. After standing still for liquid separation, the aqueous layer was extracted three times with dichloromethane (3×15 mL). After combining the organic layers, they were dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure, and the product was obtained by silica gel column chromatography, and the reaction structure was as follows:

[0038]

[0039] Using the same conditions as above, except that different compounds 1 and 2 were used, the yields of the products are shown in Table 2.

[0040] Table 2. Dearomatization of substituted indole to cyclopropane co...

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Abstract

A method for synthesizing substituted cyclopropane compounds through dearomatizing indole is characterized in that simple Ylide reacts with substituted indole under alkaline conditions to obtain various the indole-dearomatized substituted cyclopropane compounds. The method has the advantages of simple and practical operation, easily available raw materials, high yield, and good diastereoselectivity.

Description

technical field [0001] The invention relates to a compound containing substituted indole and cyclopropane, specifically a method for dearomatizing indole to synthesize substituted cyclopropane compound Background technique [0002] The dearomatization reaction of indole is widely used in the synthesis of natural products, and most indole derivatives show important biological activities [1] . Compounds containing cyclopropane structural units widely exist in nature, and cyclopropane derivatives show important biological activities due to their special structures, and many anticancer agents have their structural units. Compounds with indolenocyclopropane structures are widely used in the synthesis of medicines and pesticides because of their special structures. [2] . At present, many methods for dearomatization of indole and synthesis of cyclopropane have been developed [3] . These methods mainly use oxidants, organocatalysis or metal catalysis. (Document 1: (a) Cha, J.Y...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D209/96
CPCC07D209/96
Inventor 周永贵罗京吴波陈木旺
Owner DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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