A method for preparing 4-imidazole formaldehyde derivatives by reductive cyclization involving tmsn3

A technology of imidazole formaldehyde and cyclization reaction, applied in the direction of organic chemistry

Active Publication Date: 2018-06-08
中科榆林能源技术运营有限责任公司
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Problems solved by technology

But all these methods are rarely reported for the construction of 4-imidazole formaldehyde derivatives

Method used

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  • A method for preparing 4-imidazole formaldehyde derivatives by reductive cyclization involving tmsn3
  • A method for preparing 4-imidazole formaldehyde derivatives by reductive cyclization involving tmsn3
  • A method for preparing 4-imidazole formaldehyde derivatives by reductive cyclization involving tmsn3

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Embodiment 1

[0024] Preparation of propargyl amide 1a: react in a 100mL three-necked reaction flask, vacuumize the reaction tube and replace it with argon three times, then add 10mmol of propargylamine, dissolve it in 50mL of DCM, and then add 20mmol of Et 3 N, then slowly dropwise added 15 mmol of TsCl, stirred at room temperature for 12 hours, extracted with ethyl acetate, and recrystallized with ethanol and petroleum ether to obtain light yellow solid propargyl-p-toluenesulfonamide. 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 NaH was added, dissolved in 20mL of tetrahydrofuran, and then 5mmol of propargyl p-toluenesulfonamide was weighed, dissolved in 10mL of tetrahydrofuran, Under the condition of ℃, the solution was slowly added dropwise to the reaction system, stirred for 1h, then 7.5mmol of benzoyl chloride was added dropwise, reacted for 3h at room temperature, saturated NH 4...

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Abstract

The invention relates to a method for preparing 4-imidazole formaldehyde derivatives through reductive cyclization reaction participated by TMSN3. Concrete method is to be raw material by the propynyl amide that simple preparation obtains, take N-iodosuccinimide (NIS) as iodine source, azidotrimethylsilane (TMSN3) as reductive agent, under the condition of water as additive , a reductive cyclization reaction occurs to obtain dihydroimidazole, and then under the condition of the dehydration reagent bis[Α,Α-bis(trifluoromethyl)benzyl alcohol]diphenylsulfide, a high-yield 4-imidazole formaldehyde derivative is obtained thing. Propigylamide can be easily prepared from cheap and easy-to-obtain starting materials, and TMSN3 is used as a nitrogen source and a reducing agent at the same time, one-step reductive cyclization and intramolecular oxygen atom transfer reaction to obtain dihydroimidazole, and then a simple dehydration reaction is 4-imidazole formaldehyde derivatives can be obtained, the reaction is simple to operate, the reaction conditions are mild, and no metal catalyst is needed.

Description

technical field [0001] The present invention relates to a TMSN 3 The involved reductive cyclization reaction prepares the method for 4-imidazole formaldehyde derivative. The specific method is to be raw material by simply preparing propynyl amide, using N-iodosuccinimide (NIS) as the iodine source, azidotrimethylsilane (TMSN 3 ) is a reducing agent, and water is used as an additive condition, a reductive cyclization reaction occurs to obtain dihydroimidazole, and then under the condition of dehydration reagent bis[A, A-bis(trifluoromethyl)benzyl alcohol]diphenylsulfide 4-imidazole formaldehyde derivatives were obtained in high yield. Background technique [0002] Imidazole compounds are one of the important heterocyclic compounds, which have good physiological and pharmacological activities and widely exist in many natural products and drugs, such as Oroidin, a natural imidazole alkaloid extracted from sponges, used to lower blood pressure The drug Moxonidine etc., and th...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D233/64
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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