Synthetic method of 2-imine-1,3-oxathiole compound

Abstract

The invention provides a synthetic method of a 2-imine-1, 3-oxathiole compound. The synthetic method comprises the steps: mixing a 2-iodophenol compound, an isothiocyanate compound, alkali, copper salt, N, N, N' N'-tetramethylethylenediamine and water at the room temperature, reacting for 1-8 hours, carrying out extraction by virtue of ethyl acetate after reaction, combining organic layers, carrying out drying by virtue of anhydrous sodium sulfate, carrying out vacuum concentration to obtain a coarse product, and carrying out column chromatography isolation and purification on the coarse product to obtain the needed2-imine-1, 3-benzo oxathiole compound. Compared with the prior art, with the adoption of the synthetic method, as the water is used as a solvent, the environment is friendly; as the reaction can be carried out at the room temperature, the energy is saved, and the environment is protected; a target product is directly obtained within a short time by utilizing a one-pot method without the generation of a by-product and the needing of inert gas shielding, and the operation is simpler; the reaction is effective, the yield reaches up to 95 percent, and the synthetic method is suitable for industrial production.

Description

technical field [0001] The invention relates to the field of organic synthesis, in particular to a synthesis method of 2-imine-1,3-oxathiolene compounds. Background technique [0002] 2-imine-1,3-oxathiolene compounds play an important role in biology and medicine. Many compounds with biological activity and medicinal value contain the structural unit of 2-imine-1,3-oxathiolene. For example, 2-(2-phenylacetate methyl) imine-1,3-oxathiobenzocyclopentene, the structure is shown in Figure A below, which is often used as an agricultural chemical pesticide; it contains 2-imine- The compound of 1,3-oxathiole, whose structure is shown in Figure B below, has potential fungicidal activity; the compound whose structure is shown in Figure C below, can be used as a fungicide for agriculture and gardening, etc. Therefore, the synthesis method of 2-imine-1,3-oxathiolene compounds has attracted extensive attention of researchers. [0003] [0004] The methods for the synthesis of suc...

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Problems solved by technology

[0028] However, this type of method often selects toluene as a solvent, the reaction temperature is high, the reaction time is long, and the operation is complicated, so it needs to be carried out under the protection of an inert gas.

[0029] There are many methods for synthesizing 2-imine-1,3-oxathiolene compounds in the prior art, but some of these methods require complex synthesis steps, many side reactions, and most of the yields are relatively low; The use of highly toxic substrates or organic solvents is likely to cause environmental pollution, and most of the reaction time is long and the temperature is high; some require inert gas protection

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