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Diheterocycle compound containing 4-thiazolidinone and pyrimidine, synthetic method and application thereof

A kind of technology of thiazolidinone and synthesis method, applied in the field of 4-thiazolidinone and pyrimidine bi-heterocyclic compound and synthesis thereof

Inactive Publication Date: 2008-09-10
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] However, there are no literature reports on the synthesis and biological activity of biheterocyclic compounds containing 4-thiazolidinone and pyrimidine

Method used

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  • Diheterocycle compound containing 4-thiazolidinone and pyrimidine, synthetic method and application thereof
  • Diheterocycle compound containing 4-thiazolidinone and pyrimidine, synthetic method and application thereof
  • Diheterocycle compound containing 4-thiazolidinone and pyrimidine, synthetic method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] Example 1: Preparation of 2-[2-[(2-methylthio-4-amino-5-pyrimidine)methylene]hydrazone]-3-methyl-4-thiazolidinone

[0031] Add 0.34g (2mmol) 4-amino-2-methylthio-pyrimidine-5-aldehyde, 0.25g (2.4mmol) 4-methyl-thiosemicarbazide, 20mL ethanol and 0.42g acetic acid into a 50mL flask, The reaction was refluxed for 12 hours under stirring, and the reaction was completed. The reaction solution was concentrated to about 10 mL, cooled to room temperature, and the product was precipitated, filtered, and the product was washed with ethanol to obtain 0.44 g of white powder 1-[(2-methylthio-4- Amino-5-pyrimidine)methylene]-4-methyl-thiosemicarbazide. The yield was 86%.

[0032] 0.26g (1mmol) 1-[(2-methylthio-4-amino-5-pyrimidine) methylene]-4-methyl-thiosemicarbazide, 0.20g (1.2mmol) ethyl bromoacetate, 0.10 Add g (1.2mmol) anhydrous sodium acetate and 20mL ethanol into a 50mL flask, reflux for 10h under stirring, the reaction is over, concentrate the reaction solution to about ...

Embodiment 2

[0038] Example 2: Preparation of 2-[2-[(2-methylthio-4-amino-5-pyrimidine)methylene]hydrazone]-3-methyl-4-thiazolidinone

[0039] Get 0.26g (1mmol) 1-[(2-methylthio-4-amino-5-pyrimidine) methylene]-4-methyl-thiosemicarbazide prepared by the method of Example 1, cyclization reagent Change to 0.17g (1.2mmol) bromoacetic acid, other operations are the same as in Example 1. 2-[2-[(2-methylthio-4-amino-5-pyrimidine)methylene]hydrazone]-3-methyl - The yield of 4-thiazolidinone was 63%.

Embodiment 3

[0040] Example 3: Preparation of 1-[(2-methylthio-4-amino-5-pyrimidine) methylene]-4-methyl-thiosemicarbazide

[0041] The reaction solvent was changed to 20mL toluene, and other operations were the same as in Example 1. The yield of 1-[(2-methylthio-4-amino-5-pyrimidine) methylene]-4-methyl-thiosemicarbazide was 80% %.

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Abstract

The invention discloses a compound containing 4-thiazolinedione and pyrimidine diheterocycle, as well as a synthesis method and an application thereof. The method includes the following steps: firstly under the action of an acid reagent, an adequate reaction is carried out between 2-methylthio-4-amino-5-aldehyde pyrimidine and the 4-substituted-aminothiourea shown in formula (II) in an organic solvent A under the action of acid at circumfluence temperature, and then the reaction liquid undergoes a treatment to obtain thiosemicarbazone shown in formula (III); secondly, under the action of an alkali reagent, the thiosemicarbazone obtained in step one reacts with a cyclization reagent with the structure of X-CH2COOR' in an organic solvent B at the circumfluence temperature, and then the reaction liquid undergoes a treatment to obtain the compound containing 4-thiazolinedione and pyrimidine diheterocycle shown in formula (I). The compound containing 4-thiazolinedione and pyrimidine diheterocycle shows certain inhibitive effect against one or a plurality of plant pathogenic bacterium, and can be used as the bactericide.

Description

(1) Technical field [0001] The invention relates to a biheterocyclic compound containing 4-thiazolidinone and pyrimidine, a synthesis method and application thereof. (2) Background technology [0002] Heterocyclic compounds are the main research direction for the development of new pesticides. Among heterocyclic compounds, thiazole compounds are an important class. Currently, many commercialized fungicides, insecticides and herbicides belong to this class of compounds. For example, flufenoxil developed by Bayer Company of Germany is an acaricide, which is effective against P. ulmis and Tetranychus pests; Rice blast caused by pear spores is effective. 4-thiazolidinone derivatives have a wide range of biological activities and can be used in the fields of medicine and pesticides. For example, thiafencarb, the international common name tazimcarb, is exactly a kind of good acaricide; Domestic Shen Jianhua (CN1699354) etc. have revealed that a class of 2,3,5-trisubstituted-4-t...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D417/12A01N43/76A01P3/00C07D239/47
Inventor 沈振陆傅荣幸胡信全胡宝祥莫卫民
Owner ZHEJIANG UNIV OF TECH
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