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Tetra-substituted imidazole synthesis method

A synthesis method and compound technology, applied in organic chemistry and other directions, can solve the problems of harsh reaction conditions, large amount of catalyst, poor selectivity, etc., and achieve the effects of being conducive to industrial production, simple process flow, and mild reaction conditions.

Inactive Publication Date: 2015-10-28
NORTHWEST UNIV(CN)
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the existing methods for synthesizing tetrasubstituted imidazoles all have some disadvantages, such as poor selectivity, harsh reaction conditions, low yield, difficult raw materials, large amounts of catalysts, lack of practicability, complex catalysts, etc.

Method used

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  • Tetra-substituted imidazole synthesis method
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  • Tetra-substituted imidazole synthesis method

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Embodiment 1

[0019] Example 1 Synthesis of tetrasubstituted imidazoles: take 1a, 1n, 2a as examples to describe in detail.

[0020] Synthesis of 1,2,4-triphenyl-5-benzoyl imidazole (1a)

[0021] Add 0.6mmol N-phenylbenzamidine, 0.5mmol chalcone, 0.01mmol ferric chloride and 0.05mmol iodine into a 25mL round bottom flask containing 2mL chlorobenzene, heat to 110 o C, reacted for 10 h under an oxygen atmosphere. After the reaction (monitored by TLC), it was cooled to room temperature. Iodine was removed with saturated sodium thiosulfate solution, ethyl acetate (15 mL×3) was added three times, then washed with saturated brine, dehydrated with anhydrous sodium sulfate, concentrated and washed with ethyl acetate / petroleum ether ( 1:5) silica gel column chromatography to obtain 170 mg of a yellow solid with a yield of 85%.

[0022] Characterization data: Mp 183?184 °C; 1 H NMR (400 MHz, DMSO) δ 7.68 (t, J = 8.5 Hz, 3H), 7.51 – 7.43 (m, 5H), 7.33 (dd, J = 17.8,10.0 Hz, 4H), 7.21 (dd, J ...

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Abstract

The present invention discloses a tetra-substituted imidazole synthesis method, wherein amidine and chalcone derivatives are adopted as raw materials and chlorobenzene is adopted as a solvent. Meanwhile, ferric trichloride and iodine are adopted as catalysts. In this way, the tetra-substituted imidazole is synthesized through the oxidative cyclization reaction. The above raw materials of the method are readily available, and the operation of the method is simple. Meanwhile, the method is mild in reaction condition, high in yield and strong in practicality, thus being suitable for industrial production.

Description

technical field [0001] The invention relates to a method for synthesizing tetrasubstituted imidazoles, belonging to the field of organic chemistry. Background technique [0002] Imidazole is a five-membered aromatic heterocyclic compound containing two nitrogen atoms in the 1-position and 3-position. The derivatives with imidazole as the structural unit are widely used in the fields of chemistry, pharmacy and industry, making imidazole derivatives a nitrogen A very important class of substances in heterocyclic compounds. Especially tetrasubstituted imidazoles are found in many natural products and widely used in functional materials. At the same time, as a key intermediate in the synthesis of medicines, pesticides, dyes, and biologically active substances, tetrasubstituted imidazoles are more and more widely used. In addition, it also has good drug activity, for example: four substituted imidazole derivatives have anti-cancer, anti-tumor activity, analgesic, anti-inflammat...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D233/64C07D409/04
CPCC07D233/64C07D409/04
Inventor 李剑利朱月路李成张继东刘萍
Owner NORTHWEST UNIV(CN)
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