N-alkoxide oxo-2-triazolidone derivative, its preparation and use

A technology of thiazolidinone and alkoxycarbonyl, applied in the field of N-alkoxycarbonyl-2-thiazolidinone derivatives

Inactive Publication Date: 2005-07-27
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] However, there are no literature reports on the synthesis and biological activity of N-alkoxycarbonyl-2-thiazolidinone derivatives

Method used

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  • N-alkoxide oxo-2-triazolidone derivative, its preparation and use
  • N-alkoxide oxo-2-triazolidone derivative, its preparation and use
  • N-alkoxide oxo-2-triazolidone derivative, its preparation and use

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] Example 1 Synthesis of N-pentyloxycarbonyl-2-thiazolidinone

[0024] Add 19.8g (0.067mol) of bis(trichloromethyl)carbonate and 50ml of dichloromethane into a 250ml three-necked flask, and slowly add n-amyl alcohol (0.2mol) under stirring. Under cooling in an ice bath, a solution of triethylamine (0.2 mol) and 10 ml of dichloromethane was slowly added dropwise, maintaining the temperature between 0 and 5°C. After the dropwise addition was completed, the temperature was raised slowly and stirred at 20° C. for 2 hours. Wash with water three times (3×50ml), dry over anhydrous sodium sulfate, filter, concentrate, and distill out n-pentyl chloroformate under reduced pressure. Yield 85.6%.

[0025] 2-Thiazolidinone (5mmol) and triethylamine (0.72g, 7mmol) were dissolved in 10ml of dichloromethane and stirred. Under cooling in an ice bath, the above n-amyl chloroformate (6 mmol) was added dropwise. After the dropwise addition was completed, the reaction was carried out at 0...

Embodiment 2

[0033] Example 2 Synthesis of N-isoamyloxycarbonyl-2-thiazolidinone

[0034] Add 19.8 g (0.067 mol) of bis(trichloromethyl) carbonate and 50 ml of chloroform into a 250 ml three-neck flask, and slowly add isoamyl alcohol (0.2 mol) while stirring. Under cooling in an ice bath, a solution of pyridine (0.2 mol) and 10 ml of chloroform was slowly added dropwise, maintaining the temperature between 0 and 5°C. After the dropwise addition was completed, the temperature was raised slowly and stirred at 25° C. for 2 hours. Wash with water three times (3×50ml), dry over anhydrous sodium sulfate, filter, concentrate, and evaporate isoamyl chloroformate under reduced pressure. Yield 82.7%.

[0035] 2-Thiazolidinone (5mmol) and triethylamine (0.82g, 8mmol) were dissolved in 15ml of dichloromethane and stirred. Under cooling in an ice bath, the above-mentioned isoamyl chloroformate (6 mmol) was added dropwise. After the dropwise addition was completed, the reaction was carried out at 0-...

Embodiment 3

[0043] Example 3 Synthesis of N-butoxycarbonyl-2-thiazolidinone

[0044] N-pentanol is replaced by n-butanol, and others are the same as in Example 1 to obtain n-butyl chloroformate. Yield 88.3%.

[0045] 2-Thiazolidinone (5mmol) and pyridine (0.56g, 7mmol) were dissolved in 10ml of chloroform and stirred. Under cooling in an ice bath, the above n-butyl chloroformate (6 mmol) was added dropwise. After the dropwise addition was completed, the reaction was carried out at 0-10°C for 9 hours. Washed three times with water, dried over anhydrous sodium sulfate, filtered and concentrated. The residue was separated and purified by column chromatography [V (petroleum ether): V (ethyl acetate) = 3: 1] to obtain 0.77 g of light yellow transparent oily N-n-butoxycarbonyl-2-thiazolidinone (compound No. 6 ). The yield was 76.3%.

[0046] Elemental Analysis Values:

[0047] C H N

[0048] Measured value (%): 47.43 6.69 6.85

[0049] Calculated value (%): 47.27 6.44 6.89

...

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Abstract

A N-oxyl carbon-2-thiazolidone derivative and its production are disclosed. The production is carried out by: 2- thiazolidone derivative condensing reacting with chloro-formate under action of acid catching agent in 0-10deg.C organic solvent, after-processing and obtaining products. It achieves higher sterilizing activity.

Description

(1) Technical field [0001] The invention relates to an N-alkoxycarbonyl-2-thiazolidinone derivative, a preparation method and use thereof. (2) Background technology [0002] Heterocyclic compounds have become the mainstream in the development of new pesticides, and in heterocyclic compounds, nitrogen-containing heterocycles are the main ones. Thiazole compounds are a category that has developed rapidly in recent years, and many commercial insecticides, fungicides, and herbicides belong to this category. For example, the systemic insecticide thiazophos developed by Ishihara Industry Company of Japan has a strong ability to kill various pests that have developed resistance to traditional insecticides; Fenconazole is a systemic fungicide that inhibits the formation of infected filaments on epispora and prevents rice blast. [0003] 2-thiazolidinone is not only a useful organic intermediate, but also has bactericidal activity itself (JP53127466). At the same time, existing li...

Claims

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Application Information

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IPC IPC(8): A01N43/78C07D277/14
Inventor 翁建全沈德隆谭成侠曹耀艳
Owner ZHEJIANG UNIV OF TECH
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