1,2,4-oxadiazole-5-imine derivative and synthesis method thereof

Abstract

The invention discloses a polysubstituted 1,2,4-oxadiazole-5-imine derivative and a synthesis method thereof, and belongs to the field of organic matter synthesis, wherein the method comprises the steps: adding a solvent into a container loaded with substituted nitrone and a substituted carbodiimide compound, stirring at the reaction temperature of 25 DEG C-100 DEG C, washing with water or a saturated salt solution after the reaction is finished, then extracting with an organic solvent, drying, carrying out reduced pressure distillation and concentration to remove the solvent, and carrying outcolumn chromatography separation on the crude product to obtain the target product 1,2,4-oxadiazole-5-imine compound. The method has the advantages of no transition metal catalyst, cheap and accessible raw materials, wide reaction substrate adaptability, mild reaction conditions, favorable regioselectivity, high yield, environment friendliness and the like, and has favorable industrial application prospects.

Description

technical field [0001] The invention relates to the fields of organic synthesis, pharmaceutical intermediates and the like, and specifically relates to a 1,2,4-oxadiazole-5-imine derivative and a synthesis method thereof. Background technique [0002] The derivatives of 1,2,4-oxadiazole heterocycles are widely used in fine chemical industry, medicine, pesticide and other fields, especially in the design and synthesis of drug molecules, they are often used as bioisosteres of amide bonds and effective active groups group. The derivatives containing 1,2,4-oxadiazole heterocycle have antibacterial, anti-inflammatory, antimalarial and anticancer activities, so it is of great significance to study the synthesis of these compounds. [0003] 5-imino-1,2,4-oxadiazole contains a variety of functional groups and can be derivatized at multiple positions. It is an important class of pharmaceutical and pesticide synthetic intermediates. However, the synthesis method of this type of comp...

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Problems solved by technology

There are also reports in the literature that the corresponding 1,2,4-oxadiazole derivatives can be obtained by using α-cyanoacetamide and benzylamide under the catalysis of tetrabutylammonium fluoride or using diketene and benzylamide under the conditions of sodium methoxide catalysis. or use the semicarbazone of acetic acid high lead oxidized ketone in methylene chloride solution, the reactant directly buckles the ring to generate the oxadiazole containing imino; but because these reaction conditions are relatively harsh, the steps are longer, and the aftertreatment is loaded down with trivial details, limit its scope of application

[0004] Although the method of using 1,3-dipolar cycloaddition reaction to synthesize oxadiazole has been reported, the synthesis of multi-substituted 1,3- The reaction of 2,4-oxadiazole-5-imine derivatives is rarely reported, and the report of the product containing chiral structure is even less

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