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Preparation method of 1,5-disubsituted tetrazole compound

An azole compound and a disubstituted technology are applied in the field of preparation of 1,5-disubstituted tetrazole compounds and achieve the effects of mild conditions and simple reaction operation.

Active Publication Date: 2016-05-25
中科榆林能源技术运营有限责任公司
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Recently, transition metals such as: Cu, Ag, Au, etc. catalyzed the synthesis of tetrazole reactions have attracted the attention of scientific researchers, and related reports have been made, but all these methods are not suitable for TMSN 3 The involved amide reaction for intramolecular oxygen transfer to synthesize tetrazoles has not been reported

Method used

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  • Preparation method of 1,5-disubsituted tetrazole compound
  • Preparation method of 1,5-disubsituted tetrazole compound
  • Preparation method of 1,5-disubsituted tetrazole compound

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Embodiment 1

[0023] Synthesis steps of propynamide 1a: react in a 50mL three-necked reaction flask, vacuumize the reaction tube and replace it with argon three times, then add 15mmol of benzaldehyde, 10mmol of p-toluenesulfonamide and 20mmol of triethylorthosilicate , Reacted at 160°C for 10h, then recrystallized from ethyl acetate and petroleum ether to obtain a white solid aldimine. The reaction was carried out in a 50mL three-necked reaction flask. After the reaction tube was evacuated and replaced with argon three times, 6mmol of phenylacetylene was added and dissolved in 20mL of THF. At -78°C, 7mmol of butyllithium was slowly added dropwise to keep Stir at this temperature for 40min, then weigh 5mmol of imine and dissolve it in 20mL of THF, add dropwise to the reaction solution, rise to room temperature, react for 3h, extract with ethyl acetate, recrystallize with ethanol and petroleum ether to obtain light yellow solid propargyl base amine. The reaction was carried out in a 50mL thr...

Embodiment 2

[0028] Synthesis steps of propynamide 2a: react in a 50mL three-necked reaction flask, vacuumize the reaction tube and replace it with argon three times, then add 15mmol of o-chlorobenzaldehyde, 10mmol of p-toluenesulfonamide and 20mmol of orthosilicate Ethyl ester was reacted at 160°C for 10 h, and then recrystallized from ethyl acetate and petroleum ether to obtain aldimine as a white solid. The reaction was carried out in a 50mL three-necked reaction flask. After the reaction tube was evacuated and replaced with argon three times, 6mmol of phenylacetylene was added and dissolved in 20mL of THF. At -78°C, 7mmol of butyllithium was slowly added dropwise to keep Stir at this temperature for 40min, then weigh 5mmol of imine and dissolve it in 20mL of THF, add it dropwise to the reaction solution, rise to room temperature, react for 3h, extract with ethyl acetate, recrystallize with ethanol and petroleum ether to obtain light yellow solid propargyl base amine. The reaction was ...

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Abstract

The invention relates to a preparation method of 1,5-disubsituted tetrazole compound. The method concretely comprises the following steps: propynoic acid amide which is obtained by simple preparation is used as a raw material, in a condition with N-Iodosuccinimide (NIS), azidotrimethylsilane (TMSN3) and water, an intramolecular oxygen atom transfer reaction is carried out, and the 1,5-disubsituted tetrazole compound is obtained. Propynoic acid amide is simply prepared from cheap and easily available initial raw materials, TMSN3 is used as a nitrogen source, the one-step intramolecular oxygen atom transfer reaction is carried out, and 1,5-disubsituted tetrazole is obtained. The method has the advantages of simple operation, and mild reaction conditions without metal catalysts.

Description

technical field [0001] The invention relates to a preparation method of a 1,5-disubstituted tetrazole compound. The specific method is to be raw material by simply preparing propynamide, in N-iodosuccinimide (NIS), azidotrimethylsilane (TMSN 3 ) and water, an intramolecular oxygen atom transfer reaction occurs to obtain a 1,5-disubstituted tetrazole compound. Background technique [0002] Tetrazole, as a member of the nitrogen-containing compound, has a planar ring skeleton, and the multi-nitrogen-rich conjugated system endows the tetrazole compound with the characteristics of not only giving electrons but also accepting electrons, which makes it possible to produce a variety of Non-covalent bond interactions, such as easy formation of hydrogen bonds, coordination with metal ions, π-π stacking, electrostatic interactions, etc., thus tetrazole compounds exhibit many special properties, and are widely used in medicine, pesticides, materials science, chemical engineering, etc....

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D257/04
Inventor 万伯顺呼延成吴凡
Owner 中科榆林能源技术运营有限责任公司
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