Method for synthesizing 2-iminothiazolidine-4-one and derivatives thereof

Abstract

The invention discloses a method for synthesizing 2-iminothiazolidine-4-one and derivatives thereof. The method comprises the following steps of: reacting water or ethanol serving as a solvent and 1 molar part of thiourea or N,N'-disubstituted thiourea and 1 to 1.5 molar parts of chloroacetic acid which are taken as reaction raw materials at the temperature of between 40 and 100 DEG C for 1 to 10hours; and thus obtaining the 2-iminothiazolidine-4-one or the derivatives thereof after reaction. In the method, the water or the ethanol is taken as the solvent, and the chloroacetic acid is a reaction substrate and also a reaction catalyst; and the acidity of the chloroacetic acid is smartly utilized to self-catalyze the reaction, thiazole heterocycles can be formed through cyclization at higher reaction yield (32.5 to 86.4 percent) under the condition that additional catalysts are not used, and the process that a fussy esterification or amidation reaction is used for derivatization of thechloroacetic acid and the aftertreatment process of waste acid obtained after reaction are avoided. The method for synthesizing the 2-iminothiazolidine-4-one and the derivatives thereof is an environment-friendly synthetic process, is easy to operate, and is particularly suitable for industrialized clean production, and design thought is ingenious.

Description

technical field [0001] The invention belongs to the technical field of thiazole compound synthesis, in particular to a synthesis method of 2-iminothiazolidin-4-one and its derivatives. Background technique [0002] Most clinical drugs are chemically synthesized compounds containing heterocyclic structures. Some natural heterocyclic compounds are also commonly used clinical drugs. Many compounds related to life activities contain heterocyclic rings. In short, the activity of drugs often depends on the structure. heterocycle in . This may be due to the fact that heterocyclic compounds are less likely to be metabolized and decomposed in the body than alicyclic or aromatic ring compounds, and have better biocompatibility with the body. [0003] Heterocyclic compounds containing N and S atoms widely exist in nature and have a wide range of biological activities, especially in anti-tumor, anti-virus, anti-bacterial, anti-inflammatory, anti-diabetic, anti-psychotic, anti-histamine...

AI Technical Summary

Problems solved by technology

[0020] Thiourea and N-substituted maleamide are obtained thiazolidinone derivatives through Michael-type addition under solvent-free conditions, and the yield is higher, which belongs to a green method (Shimo, T.; Matsuda, Y.; Iwanaga, T.; etal., Heterocycles, 2007, 71 (5), 1053-1058), but there is a substituent at the 5-position in the structure of the product obtained by this method, which is not an unsubstituted active methylene group, and cannot be further processed by condensation reaction Structural modification

[0021] The above-mentioned synthetic method has more or less various defects, thereby limiting its large-scale industrialized clean production, such as the toxicity of the reagent used is relatively large, the post-treatment is loaded down with trivial details, the product does not contain methylene, and cannot be further modified, etc. (Nekrasov, D.D.; Obukhova , A.S.Chem.Heterocylclic Compd., 2006, 42, 1109)

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