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Synthesis method of polysubstituted isoxazolidine

A technology of isoxazolidine and synthesis method, which is applied in the field of biomedicine, can solve the problems of expensive, difficult to remove heavy metals, and limit the application of pharmaceutical industry, etc., and achieve the effect of cheap raw materials, good stereoselectivity of products, and wide application range of substrates

Active Publication Date: 2021-09-07
GUANGDONG UNIV OF PETROCHEMICAL TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, this method not only requires expensive catalysts, but also the residual traces of heavy metals in the product are difficult to remove, which limits its application in the pharmaceutical industry

Method used

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  • Synthesis method of polysubstituted isoxazolidine
  • Synthesis method of polysubstituted isoxazolidine
  • Synthesis method of polysubstituted isoxazolidine

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] Preparation of (E)-2,5-dibenzyl-3-phenylisoxazolidine

[0034]

[0035] Phenylacetylene (102mg, 1.0mmol), acetophenone (132mg, 1.1mmol), potassium tert-butoxide (168mg, 1.5mmol), and dimethyl sulfoxide (5mL) were sequentially added to the reaction flask, and the temperature was raised to 100°C under stirring. , keep stirring for 40 minutes. Then add N-benzylhydroxylamine (135mg, 1.2mmol) into the reaction flask, keep warm at 100°C and react for 6 hours, TLC plate, the raw material point disappears, that is, the reaction is complete, stop stirring. Add 10 mL of distilled water, adjust the pH value to neutral with dilute hydrochloric acid, extract twice with ethyl acetate, wash the organic phase with saturated NaCl solution, dry over anhydrous magnesium sulfate, remove magnesium sulfate by filtration, and remove the solvent by rotary evaporation. The obtained oil and sodium cyanoborohydride (113 mg, 1.8 mmol) were dissolved in 5 mL of methanol, and a small amount of m...

Embodiment 2

[0037] Preparation of (E)-2-benzyl-5-p-tolylmethyl-3-phenylisoxazolidine

[0038]

[0039] Add p-methylphenylacetylene (116mg, 1.0mmol), acetophenone (132mg, 1.1mmol), sodium tert-butoxide (144mg, 1.5mmol), and dimethyl sulfoxide (5mL) into the reaction flask in turn, and heat up under stirring To 100°C, keep stirring for 40 minutes. Then add N-benzylhydroxylamine (135mg, 1.2mmol) into the reaction bottle, keep warm at 100°C and react for 5 hours, TLC plate, the raw material point disappears, that is, the reaction is complete, stop stirring. Add 10 mL of distilled water, adjust the pH value to neutral with dilute hydrochloric acid, extract twice with ethyl acetate, wash the organic phase with saturated NaCl solution, dry over anhydrous magnesium sulfate, remove magnesium sulfate by filtration, and remove the solvent by rotary evaporation. The obtained oil and sodium cyanoborohydride (113 mg, 1.8 mmol) were dissolved in 5 mL of methanol, and a small amount of methyl orange ...

Embodiment 3

[0041] Preparation of (E)-2-benzyl-5-p-nitrobenzyl-3-phenylisoxazolidine

[0042]

[0043] Add p-nitrophenylacetylene (147mg, 1.0mmol), acetophenone (132mg, 1.1mmol), sodium tert-butoxide (144mg, 1.5mmol), and dimethyl sulfoxide (5mL) into the reaction flask in turn, and heat up under stirring To 110°C, keep stirring for 30 minutes. Then add N-benzylhydroxylamine (135mg, 1.2mmol) into the reaction bottle, keep warm at 110°C and react for 5 hours, TLC plate, the raw material point disappears, that is, the reaction is complete, stop stirring. Add 10 mL of distilled water, adjust the pH value to neutral with dilute hydrochloric acid, extract twice with ethyl acetate, wash the organic phase with saturated NaCl solution, dry over anhydrous magnesium sulfate, remove magnesium sulfate by filtration, and remove the solvent by rotary evaporation. The obtained oil and sodium cyanoborohydride (113 mg, 1.8 mmol) were dissolved in 5 mL of methanol, and a small amount of methyl orange i...

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Abstract

The invention provides a synthesis method of polysubstituted isoxazolidine, and relates to the technical field of biological medicines, terminal alkyne, acetophenone and N-alkyl hydroxylamine derivatives are used as reaction raw materials to react in an aprotic polar solvent in the presence of a strong base to obtain an isoxazoline derivative with a plurality of substituent groups, then reduction is performed under the action of sodium cyanoborohydride to obtain a corresponding isoxazolidine derivative with a plurality of substituent groups; the adopted raw materials are cheap, the noble metal catalyst is not needed in the reaction process, and the substrate application range is wide; the product has good stereoselectivity, and various types of (E)-2, 3, 5-trisubstituted isoxazolidine can be obtained.

Description

technical field [0001] The present invention relates to the technical field of biomedicine, more specifically, to a method for synthesizing polysubstituted isoxazolidines. Background technique [0002] Isoxazolidine, a five-membered nitrogen-oxygen heterocyclic compound, is an important class of organic compounds, and its structural fragments appear in many drug molecules. As shown below, compound 1 has antifungal activity and can effectively inhibit fungi such as Aspergillus flavus, Fusarium moniliforme and Botrydiplodia theobromae; compound 2 has antibacterial activity; compound 3 is a molecular probe for studying the mechanism of RNA transcription; compound 4 is a synthetic muscarinic receptor agonist. In addition, isoxazolidine compounds are also a very important class of organic intermediates, which are of great significance to the synthesis of other heterocyclic compounds and physiologically active natural products such as γ-amino alcohols, β-amino acids, β-amino keto...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D261/02
CPCC07D261/02
Inventor 张志华蒋达洪王煦李升亮崔宝臣李磊
Owner GUANGDONG UNIV OF PETROCHEMICAL TECH
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