3-hydroxyisothiazole derivative as well as preparation method and application thereof

A technology for hydroxyisothiazole and derivatives, which is applied in the field of 3-hydroxyisothiazole derivatives and their preparation, can solve the problems of high toxicity to aquatic organisms, long synthesis routes, complicated processes, etc., and achieves low cost, simple preparation method steps, The effect of wide application prospects

Active Publication Date: 2021-05-28
WUHAN INSTITUTE OF TECHNOLOGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Existing insecticides that act on GABA receptors, such as fipronil and lindane, have the characteristics of environmental pollution and high toxicity to aquatic organisms.
Among isothiazoles and their derivatives, many compounds have high-efficiency and broad-spectrum insecticidal, acaricidal, antibacterial and herbicidal activities, and have high agricultural value. For example, Thio-4-PIOL and its derivatives can act on insect GABA receptor, but its synthetic route is long and complicated

Method used

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  • 3-hydroxyisothiazole derivative as well as preparation method and application thereof
  • 3-hydroxyisothiazole derivative as well as preparation method and application thereof
  • 3-hydroxyisothiazole derivative as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] Preparation of 3-hydroxy-4-(2-naphthyl)-5-(4-pyridyl)-isothiazole (I-1)

[0034] The preparation of I-1 comprises the following three steps:

[0035] Step 1: Preparation of 3-benzyloxy-4-(2-naphthyl)-5-iodo-isothiazole

[0036] Add 0.66g (2.06mmol) 3-benzyloxy-4-(2-naphthyl)-isothiazole to a 50mL two-necked flask, then protect it with argon, and add 1.55mL (3.10mmol) LDA dropwise at -78°C , after stirring for 15 minutes, dissolve 0.63g (2.48mmol) iodine in 20mL tetrahydrofuran, slowly drop into the flask, and continue stirring for 30min. After the reaction was completed, 10 mL of water was added to quench, and a little solid sodium thiosulfate was added to stir for 2 h, then extracted with ethyl acetate (30 mL×3), dried over anhydrous sodium sulfate, and concentrated by filtration. Purified by column chromatography to obtain a white solid with a yield of 90.11%; the hydrogen spectrum test result of the product 1 H NMR (400MHz, CDCl 3 ): δ7.97-7.94 (m, 1H, ArH), 7.92...

Embodiment 2

[0041] Preparation of 3-hydroxy-4-(1-naphthyl)-5-(4-pyridyl)-isothiazole (I-2)

[0042] The preparation of I-2 comprises the following three steps:

[0043] Step 1: Preparation of 3-benzyloxy-4-(1-naphthyl)-5-iodo-isothiazole

[0044] Add 0.66g (2.06mmol) of 3-benzyloxy-4-(1-naphthyl)-isothiazole into a 50mL two-necked flask and protect it with argon, then add 1.55mL (3.10mmol) of LDA dropwise at -78°C After stirring for 15 minutes, dissolve 0.63g (2.48mmol) of iodine in 20mL of tetrahydrofuran, slowly drop it into the flask, and continue to stir for 30min. Extracted with ethyl acetate (30mL×3), dried over anhydrous sodium sulfate, concentrated by filtration, and purified by column chromatography to obtain a white solid with a yield of 88.65%; mp (melting point) 127-129°C; 1 HNMR (400MHz, CDCl 3 ): δ7.98-7.88(m, 2H, ArH), 7.61-7.35(m, 5H, ArH), 7.30-7.12(m, 5H, ArH), 5.37(s, 2H, CH 2 ); MS (ESI): m / z 443.95 (M+H) + .

[0045] Step 2: Preparation of 3-benzyloxy-4-(1-napht...

Embodiment 3

[0049] Preparation of 3-Hydroxy-4-(3-biphenyl)-5-(4-pyridyl)-isothiazole (I-3)

[0050] The preparation of I-3 comprises the following three steps:

[0051] Step 1: Preparation of 3-benzyloxy-4-(3-biphenyl)-5-iodo-isothiazole

[0052] After adding 0.71g (2.06mmol) of 3-benzyloxy-4-(3-biphenyl)-isothiazole into a 50mL two-necked flask and protecting it with argon, add 1.55mL (3.10mmol) dropwise at -78°C LDA, after stirring for 15 minutes, dissolve 0.63g (2.48mmol) iodine in 20mL tetrahydrofuran, slowly drop it into the flask, continue to stir for 30min, after the reaction is completed, add 10mL water to quench, add a little sodium thiosulfate solid and stir for 2h, It was extracted with ethyl acetate (30mL×3), dried over anhydrous sodium sulfate, concentrated by filtration, and purified by column chromatography to obtain a white solid with a yield of 87.34%; mp 105-107°C; 1 H NMR (400MHz, CDCl 3 )δ7.99-7.84(m, 5H), 7.59(d, J=1.6Hz, 1H), 7.57(d, J=1.6Hz, 1H), 7.55-7.46(m, 2H)...

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Abstract

The invention provides a 3-hydroxyisothiazole derivative as well as a preparation method and application thereof, and relates to the 3-hydroxyisothiazole derivative or a pharmaceutically acceptable salt, a stereoisomer, an isotope marker, a solvate, a polymorphic substance or a prodrug of the 3-hydroxyisothiazole derivative. The 3-hydroxyisothiazole derivative is a novel GABA receptor antagonist, has obvious insecticidal activity, can be further developed into an insecticide, and has wide application prospects. The general chemical structural formula of the derivative is as shown in a formula I which is described in the specification. In the formula I, R1 is an aryl or substituted aryl group; and R2 is a benzyloxy or hydroxyl group.

Description

technical field [0001] The invention relates to the technical field of heterocyclic compounds, in particular to a 3-hydroxyisothiazole derivative and its preparation method and application. Background technique [0002] Pesticides are currently developing in the direction of high efficiency, low toxicity, and environmental protection, especially in nitrogen-containing heterocyclic compounds in recent years. Existing insecticides acting on GABA receptors, such as fipronil and lindane, have the characteristics of environmental pollution and high toxicity to aquatic organisms. Among isothiazoles and their derivatives, many compounds have high-efficiency and broad-spectrum insecticidal, acaricidal, antibacterial and herbicidal activities, and have high agricultural value. For example, Thio-4-PIOL and its derivatives can act on insect GABA receptor, but its synthetic route is long and complicated. It is extremely important to study 3-hydroxyisothiazole derivatives and further d...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D417/04C07D417/14A01N43/80A01N47/02A01P7/04
CPCC07D417/04C07D417/14A01N43/80Y02P20/55
Inventor 刘根炎黄成吴贇罗晓刚吴风收巨修练
Owner WUHAN INSTITUTE OF TECHNOLOGY
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