A kind of synthetic method of myrtle alkenyl imidazo[2,1-b][1,3,4]thiadiazole compound

A technology of alkenal-based thiadiazole and alkenal-based imidazole, applied in the field of organic synthesis, can solve problems such as synthetic methods that have not been reported at home and abroad, and achieve the effects of expanding uses and improving added value

Active Publication Date: 2021-02-26
GUANGXI UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] The myrtene aldoimidazo[2,1-b][1,3,4]thiadiazole compound synthesized by the present invention is a new type of functional compound, and the substance and its synthesis method have not been reported at home and abroad so far

Method used

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  • A kind of synthetic method of myrtle alkenyl imidazo[2,1-b][1,3,4]thiadiazole compound
  • A kind of synthetic method of myrtle alkenyl imidazo[2,1-b][1,3,4]thiadiazole compound
  • A kind of synthetic method of myrtle alkenyl imidazo[2,1-b][1,3,4]thiadiazole compound

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Experimental program
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Effect test

Embodiment 1

[0024] The preparation of compound a:

[0025]

[0026] Add myrtenyl thiadiazole and 2-bromoacetophenone into the microwave reaction flask, the molar ratio is 1:1.1, add 20mL of absolute ethanol, stir the reaction under microwave conditions for 3h, then stop the reaction, the pH =2~3. The ethanol in the reaction solution was removed by rotary evaporation to obtain an orange solid, and 20 mL of ethyl acetate was added to dissolve the solid part, filtered with suction, and the filter cake was washed three times with ethyl acetate. Dissolve the obtained solid in hot ethanol to obtain a yellow solution. At this time, the pH = 2-3. Adjust the pH to 8-9 with ammonia water. Add 50 mL of ethyl acetate to the obtained solution for extraction, and successively use 5% anhydrous sodium carbonate solution. and deionized water for three times, and the obtained organic phase was rotated to evaporate the solvent to obtain compound a. m.p.93.8~95.6℃; IR(KBr,ν / cm -1 ):3017.73cm - 1(ν Ph...

Embodiment 2

[0028] Preparation of compound b

[0029]

[0030] Add myrtenyl thiadiazole and p-methoxy-2-bromoacetophenone into the microwave reaction flask, the molar ratio is 1:1.1, add 20mL of absolute ethanol, stir and react under microwave conditions for 3h Then stop the reaction, pH=2~3. The ethanol in the reaction solution was removed by rotary evaporation to obtain an orange solid, and 20 mL of ethyl acetate was added to dissolve the solid part, filtered with suction, and the filter cake was washed three times with ethyl acetate. Dissolve the obtained solid in hot ethanol to obtain a yellow solution. At this time, the pH = 2-3. Adjust the pH to 8-9 with ammonia water. Add 50 mL of ethyl acetate to the obtained solution for extraction, and successively use 5% anhydrous sodium carbonate solution. and deionized water for three times, and the obtained organic phase was spin-evaporated to obtain compound b. m.p.124.1~125.8℃; IR(KBr,ν / cm -1 ):3014.09cm -1 (ν Ph-C-H ), 2973.32cm ...

Embodiment 3

[0032] Preparation of compound c:

[0033]

[0034] Add myrtenyl thiadiazole and p-methyl-2-bromoacetophenone into the microwave reaction flask, the molar ratio is 1:1.1, add 20mL of absolute ethanol, stir and react under microwave conditions for 3h Stop the reaction, pH=2~3. The ethanol in the reaction solution was removed by rotary evaporation to obtain an orange solid, and 20 mL of ethyl acetate was added to dissolve the solid part, filtered with suction, and the filter cake was washed three times with ethyl acetate. Dissolve the obtained solid in hot ethanol to obtain a yellow solution. At this time, the pH is 2 to 3. Use ammonia water to adjust the pH to 8 to 9. Add 50 mL of ethyl acetate to the obtained solution for extraction, and successively use 5% anhydrous sodium carbonate solution. and deionized water for three times, and the obtained organic phase was spin-evaporated to obtain compound c. m.p.154.7~156.4℃; IR(KBr,ν / cm -1 ):3024.32cm -1 (ν Ph-C-H ); 2997.63...

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Abstract

A method for synthesizing a myrtleenyl imidazo[2,1-b][1,3,4]thiadiazole compound, comprising the steps of: first selectively oxidizing α-pinene to myrtenene Aldehyde, then condensed with thiosemicarbazide to obtain myrtleenyl thiosemicarbazide, further oxidized and cyclized to obtain myrtleenyl thiadiazole, and then reacted with a series of 2-bromostyrene under microwave irradiation The ketone was subjected to cyclization reaction, and the myrtenyl imidazo[2,1-b][1,3,4]thiadiazole compound was synthesized. The present invention realizes the synthesis of myrtene aldoimidazo[2,1-b][1,3,4]thiadiazole compound for the first time. The antibacterial activity test showed that myrtenyl imidazo[2,1‑b][1,3,4]thiadiazole compound had certain antibacterial activity, which expanded the application range of α‑pinene.

Description

technical field [0001] The invention relates to the technical field of organic synthesis, in particular to a novel functional compound based on α-pinene, imidazole and thiadiazole——myrtleenyl imidazo[2,1-b][1,3,4 ] The synthetic method of thiadiazole compound. Background technique [0002] Turpentine is a natural dominant biomass resource in my country, and its main component is α-pinene. α-pinene itself and its derivatives exhibit various biological activities such as herbicide, antibacterial, insecticide and repellent. Based on the modification of the four-membered ring and double bond functional group of α-pinene molecule, the synthesis of compounds with biological activity and other functions has become one of the research hotspots in organic synthetic chemistry and forest product chemistry. [0003] α-pinene can be oxidized to obtain myrtle aldehyde, also known as myrtle aldehyde. This modification only introduces an oxygen atom on the allylic methyl group of α-pinen...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D513/04A01N43/90A01P3/00
CPCA01N43/90C07D513/04
Inventor 岑波林桂汕段文贵杨钰莹
Owner GUANGXI UNIV
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