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Method for synthesizing 2H-azirine amide

A technology for acrylamide and nitrogen heterocycle, which is applied in the field of synthesizing 2H-azacycloacrylamide derivatives, can solve the problems of low yield, small substrate range, high temperature and the like, and achieves high yield and wide substrate range. Effect

Active Publication Date: 2018-01-26
NANJING UNIV OF TECH
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The yield of 2H-azacyclopropene is synthesized by ultraviolet light method, the yield is very low, and the range of applicable substrates is small; the synthesis of 2H-azacyclopropene by high temperature heating method requires a higher temperature, usually at 100°C-300°C , the scope of applicable substrates is small; the synthesis of 2H-azacyclopropene by ferrous chloride catalyzed isoxazole ring condensation, although the yield is high, the scope of applicable substrates is very small

Method used

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  • Method for synthesizing 2H-azirine amide
  • Method for synthesizing 2H-azirine amide
  • Method for synthesizing 2H-azirine amide

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Experimental program
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Embodiment 1

[0022] The first step, synthetic raw material 3-cyclohexyl-5-aminoisoxazole:

[0023]

[0024] Add sodium acetate (2mmol) and hydroxylamine hydrochloride (2mmol) in 10ml reaction tube, then add 1ml methanol, stir

[0025] Stir for one hour, then add cyclohexylformylacetonitrile (1 mmol) in methanol (1 ml) and stir for 12-24 h. After TLC monitors that the reaction is complete, transfer the reaction solution to a 100ml round-bottomed flask, remove methanol with a vacuum rotary evaporator, add 20ml of water, extract three times with ethyl acetate, each time with 10ml of ethyl acetate, combine the organic layers, and use 20ml Wash with saturated brine, dry the organic layer with anhydrous sodium sulfate, remove ethyl acetate with a vacuum rotary evaporator, and separate the product by column chromatography. The developing solvent is polar petroleum ether / ethyl acetate=4:1, and the product is light yellow Solid, yield 80%.

[0026] The H NMR spectrum of 3-cyclohexyl-5-aminoiso...

Embodiment 2

[0032] Add 3-phenylpropyl-5-aminoisoxazole (1mmol) into a 10ml reaction tube, add 2ml of absolute ethanol, add dichloro(o-isopropoxyphenylmethylene)(tricyclohexylphosphine)ruthenium (1mol%), irradiated with 36W green light for 36 hours, after the TLC monitoring reaction was complete, the reaction solution was transferred to a 100ml round-bottomed flask, and the ethanol was removed with a vacuum rotary evaporator, and the product was separated by column chromatography, and the developing agent was two Chloromethane / ethyl acetate=4:1, the product is a white solid, and the yield is 89%.

Embodiment 3

[0034] Add 3-(4-chlorophenyl)isoxazole (1mmol) into a 10ml reaction tube, add 2ml of absolute ethanol, add dichloro[1,3-bis(2-methylphenyl)-2-imidazolidine Subunit] (2-isopropoxybenzylidene) ruthenium (1mol%), irradiated with 36W green light for 32 hours, after the TLC monitoring reaction was complete, the reaction solution was transferred to a 100ml round-bottomed flask, and rotated with a vacuum Ethanol was removed by the evaporator, and the product was separated by column chromatography. The developing solvent was dichloromethane / ethyl acetate=4:1. The product was a white solid with a yield of 92%.

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Abstract

The invention relates to a method for synthesizing 2H-azirine amide. 5-aminoisoxazole as a raw material is added to a reaction solvent, the Hoveyda-Grubbs Catalyst is then added, the materials are subjected to a catalytic reaction under green light illumination, the reaction solvent is removed from an obtained reaction liquid, the liquid is purified, and a product is obtained. The synthesis methodadopts quite mild required conditions and is green and high in yield, and the range of applicable substrates is wide, for example, various substituted phenyl groups, heterocyclic rings, olefins and alkanes can be adopted in the 2nd position of a three-membered ring of 2H-azirine amide, methyl, allyl, phenyl and 1-phenyl allyl groups can be adopted in the 3rd position, and arene, alkane or acyl substituted amine can be adopted for amide.

Description

technical field [0001] The invention relates to a method for synthesizing 2H-azacycloacrylamide derivatives, which belongs to the technical field of organic synthesis methodology. Background technique [0002] The 2H-azacyclopropene structure in 2H-azacycloacrylamide derivatives exists in many natural products and is a common skeleton of many natural product drugs. for example: [0003] [0004] 2H-Aziridines, as a class of highly reactive compounds, have their structures in many natural products and drugs. In organic synthesis, 2H-azacyclopropene can be used as a reaction intermediate or a reaction precursor to synthesize various useful heterocyclic compounds, such as pyridines, furans, pyrroles, and indoles. At present, there are three main methods for synthesizing 2H-nitroheterocyclic acrylamide, ultraviolet light, high temperature heating, and ferrous chloride catalyzed isoxazole ring condensation. The yield of 2H-azacyclopropene is synthesized by ultraviolet light...

Claims

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Application Information

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IPC IPC(8): C07D203/04
Inventor 姜耀甲戈云裴冰冰丁佳罗德平
Owner NANJING UNIV OF TECH
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