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Preparation method of 2,4,5-trisubstituted imidazole compound

A compound, a technology for imidazole, which is applied in the field of preparation of imidazole compounds, can solve the problems of poor applicability of different functional groups, difficult to obtain raw materials, low product yield and the like, and achieves the effects of easy operation of steps, cheap reaction raw materials and high yield.

Inactive Publication Date: 2015-08-19
ZHEJIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0016] Although there are many reports on the synthesis of 2,4,5-trisubstituted imidazoles, the known synthetic methods still have problems such as difficult access to raw materials, use of highly toxic catalysts, low product yields, and poor applicability to different functional groups. , the above factors make it imperative to develop a novel preparation method for 2,4,5-trisubstituted imidazoles

Method used

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  • Preparation method of 2,4,5-trisubstituted imidazole compound
  • Preparation method of 2,4,5-trisubstituted imidazole compound
  • Preparation method of 2,4,5-trisubstituted imidazole compound

Examples

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Effect test

Embodiment 1

[0048] Example 1: Preparation of 5-methyl-4-phenyl-1H-imidazole

[0049] 1. Preparation of raw material 2-methyl-2-nitro-3-phenyloxirane

[0050] Add 2.1g (20mmol) of benzaldehyde and 9.0ml (100mmol) of nitroethane into a three-necked flask, and slowly add Et 3N 0.3ml (2mmol). After the addition was complete, stir at room temperature under nitrogen protection for 18h. After the disappearance of raw materials detected by the TLC plate, the excess solvent was evaporated under reduced pressure, and the crude product α-nitroalcohol was directly dissolved in dichloromethane, and then 7.4 mL (42 mmol) of N,N-diisopropylethylamine and formaldehyde were added sequentially. Sulfonyl chloride 1.9 mL (24 mmol), after the addition, the reaction gradually returned to room temperature. After the TLC plate detected that the raw materials disappeared, the reaction system was extracted with dichloromethane, and the organic phase was washed twice with 10ml of 2M dilute hydrochloric acid and o...

Embodiment 2

[0075] Example 2, 5-ethyl-4-phenyl-1 H- Preparation of imidazole

[0076] Replace 2-methyl-2-nitro-3-phenyloxirane with 2-ethyl-2-nitro-3-phenyloxirane, the molar weight remains the same, and the rest are the same as in Example 1. 5-Ethyl-4-phenyl-1 was obtained as a white solid H- Imidazole 163mg, yield 95%. Its structural formula is:

[0077]

[0078] 1 H NMR (500 MHz, DMSO) δ 7.61 (s, 1H), 7.58 (dd, J = 8.1, 1.0 Hz, 2H), 7.39 (dd, J = 10.7, 4.9 Hz, 2H), 7.25-7.19 (m, 1H), 2.76 (q, J = 7.5 Hz, 2H), 1.22 (t, J = 7.5 Hz, 3H). 13 C NMR (125 MHz, DMSO) δ 134.78, 134.52, 128.88, 126.60, 126.19, 19.49, 14.61. HRMS (ESI): m / z calcd for C 11 h 13 N 2 [M+H] + :173.1073, found: 173.1073.

Embodiment 3

[0079] Example 3, 4-(4-chlorophenyl)-5-methyl-1 H - Preparation of imidazole

[0080] Replace 2-methyl-2-nitro-3-phenyloxirane with 3-(4-chlorophenyl)-2-methyl-2-nitrooxirane, the molar weight remains unchanged, and the rest With embodiment 1. The product 4-(4-chlorophenyl)-5-methyl-1 was obtained as a yellow solid H -Imidazole 171 mg, yield 89%. Its structural formula is:

[0081]

[0082] 1 H NMR (500 MHz, DMSO) δ 12.11 (s, 1H), 7.64 (d, J = 8.4 Hz, 2H), 7.60 (s, 1H), 7.43 (d,J = 8.4 Hz, 2H), 2.38 (s, 3H). 13 C NMR (125 MHz, DMSO) δ 134.40, 130.36, 128.80, 127.78, 12.21. HRMS (ESI): m / z calcd for C 10 h 10 ClN 2 [M+H] + :193.0527, found: 193.0537.

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Abstract

The invention provides a preparation method of a 2,4,5-trisubstituted imidazole compound. The 2,4,5-trisubstituted imidazole compound is synthesized through a reaction of alpha-nitro epoxide with an amidine compound and an alkali at room temperature via a one-pot process. The synthetic method has the characteristics of mild conditions, high yield, and cheap and easily available raw materials, and is a simple and feasible method for efficiently synthesizing the 2,4,5-trisubstituted imidazole compound. The preparation method also has the advantages of reasonable design, easily available raw materials, easy and convenient operation, mild conditions and high yield.

Description

technical field [0001] The invention belongs to a compound synthesis method, and mainly relates to a preparation method of 2,4,5-trisubstituted imidazole compounds. Background technique [0002] As a class of five-membered aromatic heterocyclic compounds, imidazoles are widely used in many fields such as medicine, pesticides, materials, and fine chemicals. Multi-substituted imidazoles, especially 2,4,5-trisubstituted imidazoles, are a very important class of imidazoles. Plays a crucial role in the synthesis of inflammatory drugs. [0003] Since 2,4,5-trisubstituted imidazole compounds have very important application value, their synthesis methods have always been a hot spot in the field of synthesis. In recent years, new methods have emerged one after another, among which the following are representative. [0004] (1) Microwave-assisted synthesis of polysubstituted imidazoles proposed by Scott E. Wolkenberg et al. (Scott E. Wolkenberg, David D. Wisnoski, William H. Leister...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D233/58C07D233/64C07D409/04
CPCC07D233/58C07D233/64C07D409/04
Inventor 郭晓邵加安俞永平
Owner ZHEJIANG UNIV
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