3-azabicyclo [4,1,0] heptyl aldehydes and preparation method thereof

A technology of azabicyclo and heptanal, which is applied in the field of metal-catalyzed carbene [2+1] cycloaddition reaction, can solve the problems of limited preparation methods, and achieve the effects of difficult preparation, simple operation and novel structure

Inactive Publication Date: 2015-05-20
CHANGZHOU UNIV
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  • Abstract
  • Description
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  • Application Information

AI Technical Summary

Problems solved by technology

At present, the preparation methods of such compounds are limited, mainly the oxidative cyclization of enyne compounds under the action of metal catalysts.

Method used

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  • 3-azabicyclo [4,1,0] heptyl aldehydes and preparation method thereof
  • 3-azabicyclo [4,1,0] heptyl aldehydes and preparation method thereof
  • 3-azabicyclo [4,1,0] heptyl aldehydes and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] Mix 2 mmol of sulfonyltriazole 1a and 0.01 mmol of rhodium acetate in 10 ml of dichloromethane and stir at a temperature of 40 degrees. After 5 hours, stop heating, add 2 ml of methanol, 5 mmol of potassium carbonate and 0.5 mL of water, stirred at room temperature for 10 hours. Extract three times with the organic solvent ethyl acetate, combine the organic phases and wash with saturated brine, then dry with anhydrous sodium sulfate, evaporate the solvent under reduced pressure, use ethyl acetate and petroleum ether as eluents for the residue, and perform silica gel column chromatography After separation and purification, the corresponding azabicyclic aldehyde 2a was obtained (see Table 1). Alternatively, after the reaction is completed, the organic solvent is evaporated under reduced pressure, and the residue is directly separated on a silica gel column.

Embodiment 2

[0028] Mix 2 mmol of sulfonyltriazole 1e and 0.1 mmol of rhodium acetate in 10 ml of toluene and stir at a temperature of 120°C. After 10 minutes, stop heating and add 2 ml of methanol, 5 mmol of potassium carbonate and 0.5 ml of water , stirred at room temperature for 10 hours. Extract three times with the organic solvent ethyl acetate, combine the organic phases and wash with saturated brine, then dry with anhydrous sodium sulfate, evaporate the solvent under reduced pressure, use ethyl acetate and petroleum ether as eluents for the residue, and perform silica gel column chromatography Separation and purification gave the corresponding indole aldehyde 2e (see Table 1). Alternatively, after the reaction is completed, the organic solvent is evaporated under reduced pressure, and the residue is directly separated on a silica gel column.

Embodiment 3

[0030] Mix 2 mmol of sulfonyltriazole 3a and 0.01 mmol of rhodium acetate in 10 ml of dichloromethane and stir at a temperature of 40°C. After 5 hours, stop heating, add 2 ml of methanol, 5 mmol of potassium carbonate and 0.5 mL of water, stirred at room temperature for 10 hours. Extract three times with the organic solvent ethyl acetate, combine the organic phases and wash with saturated brine, then dry with anhydrous sodium sulfate, evaporate the solvent under reduced pressure, use ethyl acetate and petroleum ether as eluents for the residue, and perform silica gel column chromatography Separation and purification yielded the corresponding indole aldehyde 4a (see Table 2). Alternatively, after the reaction is completed, the organic solvent is evaporated under reduced pressure, and the residue is directly separated on a silica gel column.

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Abstract

The invention discloses 3-azabicyclo [4,1,0] heptyl aldehydes, specifically 3-azabicyclo [4,1,0]-6-aldehyde and 3-azabicyclo [4,1,0]-1-aldehyde, and a preparation method thereof and belongs to the technical field of chemical pharmaceuticals and fine chemical preparation. A cyclopropano-aza cycle is an important organic compound; according to the method, metal catalyzed sulfonyl triazole is decomposed into metal carbene, then, metal carbene [2+1] cycloaddition reaction occurs, further hydrolysis is carried out, and then, 3-azabicyclo [4,1,0] heptyl aldehydes are obtained, so that the effective synthesis of high-added-value cyclopropano-aza cycle is realized, a new technical route is provided for preparing related derivatives, and the application in the fields of chemical pharmaceuticals and fine chemical industry is broad.

Description

technical field [0001] The invention belongs to the technical field of chemical pharmacy and fine chemical preparation, namely the one-pot method for preparing 3-azabicyclo[4,1,0]heptanal, and in particular relates to metal-catalyzed carbene[2+1]cycloaddition reaction. The invention provides a new technical route and design strategy for efficiently preparing functionalized azabicycles, and has wide applications in the fields of chemical pharmacy and fine chemical industry. Background technique [0002] Azabicycles are an important class of organic compounds. Many compounds containing this type of structure have special chemical and biological activities, and also exist in many natural products and drug molecules. Among them, cyclopropane azabicycles have attracted much attention in recent years. . At present, the preparation methods of this kind of compounds are limited, mainly the oxidative cyclization of enyne compounds under the action of metal catalysts. The present in...

Claims

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Application Information

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IPC IPC(8): C07D221/04
CPCC07D221/04
Inventor 徐华栋贾志宏徐科沈美华
Owner CHANGZHOU UNIV
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