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Bi-triazole compound, preparation method and application thereof

A compound, bitriazole technology, applied in the field of bitriazole compound and its preparation, to achieve the effect of simple preparation

Inactive Publication Date: 2005-10-26
WUHAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

And the bitriazole compound synthesized by this patent has not yet been reported

Method used

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  • Bi-triazole compound, preparation method and application thereof
  • Bi-triazole compound, preparation method and application thereof
  • Bi-triazole compound, preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] 5-Azido-1,2,4-triazole-3-acylmethyl ester (50 mg, 0.297 mmol) was placed in a two-necked flask, vacuumized on an oil pump for 20 minutes, and then 10 mL of a mixed solvent (THF / H 2 O=1 / 4), a colorless and transparent solution was obtained. Then, propynyl acetate (35 mg, 0.36 mmol) was added under the protection of Ar gas. Separately, copper sulfate pentahydrate (11.8 mg, 0.047 mmol) and sodium ascorbate (29.5 mg, 0.148 mmol) were dissolved in 200 μL of water, and then injected into the above reaction system. After reacting at 80° C. for 1 hour, the reaction was stopped. At this time, the reaction system was a yellow turbid liquid. After the solvent was distilled off under reduced pressure, a yellow solid was obtained. The product was separated by column chromatography (CH 2 Cl 2 / MeOH=30 / 1), the obtained product (1a) was 73.1 mg of white solid after vacuum drying, and the yield was 92.4%.

[0033] 1 H NMR (300MHz, DMSO-d 6 ): δ8.79(s, 1H), 5.22(s, 2H), 3.96(s, 3H)...

Embodiment 2

[0035] 5-azido-1,2,4-triazole-3-acylmethyl ester (50mg, 0.297mmol) was placed in a two-necked flask, vacuumized on an oil pump for 20 minutes, and then 5mL of a mixed solvent (THF / H 2 O=1 / 2), the raw materials were dissolved to obtain a colorless and transparent solution. Then p-pentanephenylacetylene (50mg, 0.297mmol) was added under the protection of Ar gas. Separately, copper sulfate pentahydrate (11.8 mg, 0.047 mmol) and sodium ascorbate (29.5 mg, 0.148 mmol) were dissolved in 200 μL of water, and then injected into the above reaction system. After reacting at 60° C. for 2 hours, the reaction was stopped. At this time, the reaction system was a brownish-yellow turbid liquid. After directly distilling off the solvent under reduced pressure, a brownish-yellow solid was obtained. The product was separated by column chromatography (CH 2 Cl 2 / MeOH=30 / 1), the obtained product (1b) was 82.2 mg of white solid after vacuum drying, and the yield was 81.2%.

[0036] 1 H NMR (30...

Embodiment 3

[0038] Put 5-azido-1,2,4-triazole-3-acylmethyl ester (50 mg, 0.297 mmol) in a two-necked flask, vacuumize it on an oil pump for 20 minutes, then add 12 mL of tetrahydrofuran, the raw material is dissolved to obtain a colorless Clear solution. Then cyclohexanol alkyne (54.7 mg, 0.44 mmol) was added under the protection of Ar gas. Separately, copper sulfate pentahydrate (11.8 mg, 0.047 mmol) and sodium ascorbate (29.5 mg, 0.148 mmol) were dissolved in 200 μL of water, and then injected into the above reaction system. After reacting at 90° C. for 2 hours, the reaction was stopped. At this time, the reaction system was a light yellow turbid liquid. After the solvent was distilled off under reduced pressure, a yellow solid was obtained. The product was separated by column chromatography (CH 2 Cl 2 / MeOH=30 / 1), the obtained product (1c) was 67.5 mg of white solid after vacuum drying, and the yield was 77.7%.

[0039] 1 H NMR (300MHz, DMSO-d 6 ): δ8.41(s, 1H), 5.07(br s, 1H), 3...

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Abstract

The present invention relates to a triazole compound. Said invention provides its general formula. Its preparation method includes the following steps: using 5-triazo-1,2,4 triazol-3-acyl methyl ester and propiolic alcohol ester acetate, p-amyl phenylacetylene, syclohexanol alkyne, cyclohexene alkyne or methoxyphenyl acetylene, and making them be reacted in the tetrahydrofuran or mixed solvent of tetrahydrofuran and water at 10-100 deg.C under the action of Cu(I) catalyst so as to obtain the required triazole compound. Said triazole compound has the activity for directly inhibiting plant virus, in particular inhibiting tobacco mosaic virus.

Description

technical field [0001] The invention relates to a bitriazole compound, a preparation method and application thereof, and belongs to the fields of organic chemistry and biochemistry. Background technique [0002] Plant viral diseases are known as "plant cancers". The proportion of plant diseases is second only to fungal diseases, and they pose a serious threat to agricultural production. Related research is in the ascendant (Whitham, 2004). It is estimated that the annual loss caused by tobacco mosaic virus (Tobacco mosaic virus, TMV) in the world is more than 100 million US dollars. Since viruses are obligately parasitic in plant cells, the materials, energy and places required for their replication are completely dependent on the host, and plants do not have a complete immune metabolism system, making the prevention and treatment of plant virus diseases particularly difficult. In order to effectively prevent and treat plant virus diseases, people have carried out beneficia...

Claims

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Application Information

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IPC IPC(8): C07D403/04
Inventor 曲凡歧夏熠范志金李蔚彭玲
Owner WUHAN UNIV
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