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3-(4-methyl-1, 2, 3-thiadiazole-5-yl)-1, 5-diketone derivatives as well as preparation method and application thereof

A technology of thiadiazole and its derivatives, applied in the field of 3--1

Inactive Publication Date: 2012-08-15
NANKAI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] 1,2,3-Thiadiazole compounds also have a wide range of biological activities. For related patents and literature summaries, see Bakulev, et al.Newyork: John Wiley&Sons, Inc, 2004 monograph. 1,3,4-thiadiazole derivatives, 1,2,5-thiadiazole derivatives and 1,2,4-thiadiazole derivatives, and for 1,2,3-thiadiazole derivatives There are relatively few reports on the activity of

Method used

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  • 3-(4-methyl-1, 2, 3-thiadiazole-5-yl)-1, 5-diketone derivatives as well as preparation method and application thereof
  • 3-(4-methyl-1, 2, 3-thiadiazole-5-yl)-1, 5-diketone derivatives as well as preparation method and application thereof
  • 3-(4-methyl-1, 2, 3-thiadiazole-5-yl)-1, 5-diketone derivatives as well as preparation method and application thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0029] Preparation of 4-methyl-1,2,3-thiadiazole-5-methanol II

[0030] In a 500 ml round bottom flask, add 30 g of 4-methyl-1,2,3-thiadiazole-5-ethyl carboxylate and 240 ml of ethanol. Under ice bath stirring, add 13.2 g of boron in batches After adding sodium hydride, continue to stir in an ice bath for 1 hour, remove the ice bath and stir overnight. After monitoring the completion of the reaction, filter with suction to remove the solvent under reduced pressure, extract with ethyl acetate, dry with anhydrous sodium sulfate, and filter with suction After removing the anhydrous sodium sulfate, concentrating under reduced pressure to remove the solvent, the compound was separated and purified by column chromatography with a volume ratio of petroleum ether: ethyl acetate as the eluent of 2:1 to obtain 17.50 g of pale yellow liquid with a yield of 77%.

Embodiment 2

[0032] Preparation of 4-methyl-1,2,3-thiadiazole-5-carbaldehyde III

[0033] In a 500 ml round bottom flask, add 10 g of 4-methyl-1,2,3-thiadiazole-5-methanol, 300 ml of dichloromethane, add 26.48 g of PCC in batches, and stir overnight at room temperature to monitor the completion of the reaction Then, the compound was separated and purified by suction filtration, concentrated under reduced pressure to remove the solvent, and the compound was separated and purified by column chromatography with a volume ratio of petroleum ether: ethyl acetate as an eluent of 8:1 to obtain 6.40 g of a brown liquid with a yield of 65%.

Embodiment 3

[0035] Compound DGD-1: Synthesis and structure identification of 1,5-diphenyl-3-(4-methyl-1,2,3-thiadiazol-5-yl)-1,5-pentanedione

[0036] In a 50 ml round-bottom flask, add 0.5 g of 4-methyl-1,2,3-thiadiazole-5-carbaldehyde, 0.94 g of acetophenone, and 20 ml of methanol, and then dropwise add 1.1 g of hydroxide A 50% potassium hydroxide solution prepared with potassium and 1.1 ml of water was stirred at room temperature for 5 hours. After monitoring the completion of the reaction, add dilute hydrochloric acid solution to neutralize the excess potassium hydroxide to pH 7, and concentrate under reduced pressure to remove the solvent. The compound was separated and purified by column chromatography with an eluent of 8:1 petroleum ether: ethyl acetate to obtain 0.70 g of white solid, melting point: 105-107 degrees Celsius, yield 51%. Nuclear magnetic data (CDCl 3 , Chemical shift): 2.805 (s, 3H, CH 3 ), 3.464 (dd, J=7.2Hz, 18Hz, 2H, CH 2 ), 3.628 (dd, J=6.0Hz, 17.6Hz, 2H, CH 2 ), 4....

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Abstract

The invention provides 3-(4-methyl-1, 2, 3-thiadiazol-5-yl)-1, 5-diketone derivatives as well as a preparation method and application thereof and relates to heterocyclic compounds containing 1, 2, 3-thiadiazole. The compounds have a chemical structure general formula as shown in V. The invention discloses the structure general formula and the synthetic method of the compounds, the application of the compounds as bactericides and a processing technology for preparing the bactericides, plant virtues resisting agents and plant activators by mixing the compounds with agriculturally acceptable auxiliaries or synergists. The invention further discloses the application of combination of the compounds, commercial insecticides, the bactericides, the plant virtues resisting agent and the plant activators in the aspects of preventing and controlling agricultural, forestry and horticultural diseases, insect pests and virus diseases and the preparation method of the compounds.

Description

Technical field [0001] The technical scheme of the present invention relates to compounds containing 1,2-diazole, in particular to 3-(4-methyl-1,2,3-thiadiazol-5-yl)-1,5-dione derivatives. Background technique [0002] The Michael reaction is an important reaction for the formation of carbon-carbon bonds and the growth of carbon chains. It has a wide range of reaction substrates and is widely used in organic synthesis. Robinson used the Michael reaction to synthesize a 6,6-fused ring system during the synthesis of steroids, which is one of the most successful application cases of the Michael reaction (Rapson, W.S., etc., J. Chem. Soc. 1935, 1285). In the total synthesis of (+)-Dihydromevinolin, Hanessian et al. introduced the Michael reaction to complete the synthesis of the parent structure (Hanessian, S., et al. J. Org. Chem. 1990, 55: 5755), and the synthesis of other drugs such as antidepressants Paxil active ingredients (-)-Paroxetin and (+)-Femoxetin (Brandau, S., etc. Ang...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D285/06A01N43/828A01P3/00A01P7/04A01P7/02A01P1/00A01P21/00
Inventor 范志金国丹丹毛武涛王盾王治文赵晖李岳东房震姬晓恬华学文特蒂安娜·卡林丽娜莫则林·余瑞·余瑞维奇贝尔斯卡娅·娜特丽娅·帕沃洛娃巴库勒夫·瓦西里耶·阿勒克什维奇
Owner NANKAI UNIV
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