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A New Method for Preparation of Oxazole Derivatives

A technology of derivatives and oxazole, which is applied in the field of chemical synthesis of oxazole derivatives, can solve the problems of unfavorable environmental protection and large-scale industrial production, simple operation steps, harm to human body and environment, etc. Cheap and easy to get, avoid the effect of catalyst

Active Publication Date: 2017-02-22
SHANGHAI DINGYA PHARM CHEM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0006] But above-mentioned reaction needs to use sodium nitrite, and sodium nitrite is carcinogen, easily causes harm to human body and environment; Need to use H in the dehydration cyclization step simultaneously 2 SO 4 ,P 2 o 5 , SOCl 2 or PCl 5 etc. are used as dehydrating agents, resulting in difficulties in wastewater treatment, which is not conducive to environmental protection and large-scale industrial production; the final operation steps are not simple enough

Method used

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  • A New Method for Preparation of Oxazole Derivatives
  • A New Method for Preparation of Oxazole Derivatives

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] The preparation of embodiment one 1-(oxazole-2)-ethanone

[0027] .

[0028] Add 5.0 g of p-toluenesulfonylmethyl isonitrile (0.0256 mol) into a 250 mL three-necked flask, add 50 mL of dichloromethane, stir and mix evenly, add 2.2 g of acetyl chloride (0.0278 mol) dropwise under ice-bath conditions, After the addition, stir at room temperature until the reaction is complete. Concentrate the reaction solution to remove dichloromethane, add 50mL tetrahydrofuran, cool to 0°C in an ice bath, add 3.0g formaldehyde (0.1mol) to the system, and then add 12.9g DBU (0.0514mol) dropwise, keeping the reaction temperature not exceeding 0°C , Stir at 0°C for 4 hours after the addition, and then stir at room temperature until the reaction is complete. Then add 50mL saturated saline to the system, let stand to separate the layers, extract with ether three times, combine the organic phases, wash with water, wash with brine, dry over anhydrous sodium sulfate, filter, keep the tempera...

Embodiment 2

[0030] Example two (oxazol-2-yl) cyclopropyl ketone

[0031] .

[0032]Add 5.0g of p-toluenesulfonylmethyl isonitrile (0.0256mol) into a 250mL three-necked flask, add 50mL of dichloromethane, stir and mix evenly, and dropwise add 3.3g (0.0310mol) of cyclopropylmethyl in an ice bath Acyl chloride, after the addition, stir at room temperature until the reaction is complete. Concentrate the reaction solution to remove dichloromethane, add 50 mL of tetrahydrofuran, cool to 0 °C in an ice bath, add 5.6 g (0.187 mol) of formaldehyde to the system, and then dropwise add 16.0 g of DBU (0.0638 mol), keeping the reaction temperature not exceeding 0 °C, Stir at 0°C for 4 hours after the addition, and then stir at room temperature until the reaction is complete. Then add 50mL saturated saline to the system, let stand to separate the layers, extract with ether three times, combine the organic phases, wash with water, wash with brine, dry over anhydrous sodium sulfate, filter, keep the ...

Embodiment 3

[0034] Example three oxazol-2-yl-(phenyl)methanone

[0035] .

[0036] Add 40mL toluene and 5.0g p-toluenesulfonylmethyl isonitrile (0.0256mol) to a 250mL three-necked flask in sequence, stir and mix evenly, add 4.3g benzoyl chloride (0.0305mol) dropwise under ice bath conditions, and complete the addition After that, stir at room temperature for 30 minutes, then raise the temperature to 50°C and stir until the reaction is complete. Concentrate the reaction solution to remove toluene, add 70mL of acetonitrile, cool in an ice bath to below 0°C, add 5.0g of formaldehyde (0.167mol) to the system, and then add 7.1g of potassium carbonate (0.0514mol), keep the reaction temperature not exceeding 0°C, After the addition, the temperature did not exceed 0°C and stirred for 3-4 hours, then stirred at room temperature until the reaction was complete, concentrated to remove acetonitrile, added 50 mL of water, extracted with ether three times, combined the organic phases, washed with wa...

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Abstract

The invention particularly relates to a method for synthesizing oxazole derivative, belonging to the field of synthesis of heterocyclic compounds. The technical scheme is as follows: the method comprises the following steps: reacting the raw material tosyl methyl isonitrile derivative disclosed as Formula (I) with acyl chloride disclosed as Formula (II) to obtain alpha-ketoimine chloride disclosed as Formula (III); and reacting the intermediate alpha-ketoimine chloride disclosed as Formula (III) with aldehyde (IV) in the presence of a protonic solvent and alkali to obtain 2-substituted oxazole (V). Compared with the prior art, the method uses cheap and accessible raw materials, avoids using the catalyst, lowers the cost, reduces the environmental pollution, has the advantage of mild reaction conditions, and is simple to operate and beneficial to industrial production.

Description

technical field [0001] The present invention relates to the synthesis of heterocyclic compounds, in particular to a new method for the chemical synthesis of oxazole derivatives. Background technique [0002] Oxazole compounds are an important class of heterocyclic compounds, which contain two kinds of heteroatoms, oxygen and nitrogen, can undergo a variety of non-covalent bond interactions, and have some special properties. Therefore, they are used in pharmaceutical intermediates, drug synthesis, Pesticides, chemistry, materials science and many other fields have a wide range of application value. In addition, as a bioelectronic isostere, the oxazole ring can be widely used to replace triazole, imidazole, pyrazole, thiazole and other groups to design and develop new drugs, which can improve the biological activities of compounds (such as antifungal, antibacterial, anticancer , anti-virus, anti-tuberculosis, hypoglycemic, anti-convulsant, anti-inflammatory and analgesic, etc...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D263/32C07D413/04
CPCC07D263/32C07D413/04
Inventor 阮诗文严恭超徐丽萍阮晓娜
Owner SHANGHAI DINGYA PHARM CHEM CO LTD