Preparation method polysubstituted imidazole derivatives

A polysubstituted and derivative technology is applied in the field of preparation of polysubstituted imidazole derivatives, which can solve the problems of complicated synthesis steps, harsh reaction conditions, limited substituents, etc., and achieves easy availability of raw materials, simple operation, and cheap reaction raw materials. easy-to-get effect

Inactive Publication Date: 2015-04-22
ZHEJIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] There are many synthetic methods for multi-substituted imidazole derivatives, the common ones are constructed by Ugi multi-component and Davidson ring closure method, or by starting raw materials, such as amides, imines, cyano groups, amino acids, isonitriles, etc., by A series of catalysis, cyclization, and isomerization to obtain the target compound, but in the methods reported so far, either the synthesis steps are cumbersome, the raw materials are difficult to obtain, the reaction conditions are harsh, the need for metal catalysis, or the substituents are limited. Development of a new class of methods for the construction of polysubstituted imidazoles

Method used

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  • Preparation method polysubstituted imidazole derivatives
  • Preparation method polysubstituted imidazole derivatives
  • Preparation method polysubstituted imidazole derivatives

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] Example 1: 2,4-Diphenyl-5-carbonyl-1 H - Preparation of imidazole

[0029] 1. Raw material 1: preparation of ethyl benzimide

[0030] Add 3.43ml (33.6mmol) of benzonitrile and 15.7ml (33.6mmol, 1.0eq.) of ethanol to the three-necked flask, slowly add 18.7ml (33.6mmol, 1.0eq.) of acetyl chloride dropwise under ice-bath conditions, After the addition was complete, it was stirred overnight at room temperature. After the disappearance of the raw materials detected by the TLC plate, the reaction system was extracted with ethyl acetate, and the solvent was evaporated under reduced pressure to obtain a light yellow liquid, which was directly used in the next reaction with a yield of 92%.

[0031] 2. Raw material 2: Preparation of ethyl 2-azido-3-phenylacrylate

[0032] Add sodium 713mg (31mmol) slowly to a three-necked bottle filled with 20ml of ethanol to make sodium ethoxide. After returning to room temperature, transfer to a low temperature environment of -15°C, slowl...

Embodiment 2

[0038] Example 2: 2-Phenyl-4-methoxyphenyl-5-carbonyl-1 H - Preparation of imidazole

[0039] The operation process is the same as in Example 1, except that ethyl 2-azido-3-methoxyphenylacrylate is used instead of ethyl 2-azido-3-phenylacrylate, and the reaction is subjected to silica gel column chromatography to obtain a yellow solid. The rate is 76%, melting point: 122.9-123.3 ℃.

[0040] Its structural formula is:

[0041]

[0042] 1 H NMR (500 MHz, CDCl 3 ) δ 10.18 (s, 1H), 7.97 (m, 3H), 7.48 -7.36 (m, 6H), 4.35 (q, J = 7.1 Hz, 2H), 1.69 (s, 3H), 1.33 (t, J = 7.1 Hz, 3H); 13 C NMR (125 MHz, CDCl 3 for C 19 h19 N 2 o 3 [M+H] + = 323.1390, found 323.1394.

Embodiment 3

[0043] Example 3: 2-Phenyl-4-(2-furan)-5-carbonyl-1 H - Preparation of imidazole

[0044] The operation process is the same as in Example 1, except that ethyl 2-azido-3-(2-furan)acrylate is used instead of ethyl 2-azido-3-phenylacrylate, and the reaction is subjected to silica gel column chromatography to obtain a yellow solid, which is collected as The rate is 52%, and the melting point is 117.7-118.0°C.

[0045] Its structural formula is:

[0046]

[0047] 1 H NMR (500 MHz, CDCl 3 ) δ 10.19 (s, 1H), 7.98 (m, 3H), 7.44 (m, 5H), 4.35 (q, J = 7.1 Hz, 2H), 1.33 (t, J = 7.1 Hz, 3H); 13 C NMR (125 MHz, CDCl 3 for C 16 h 15 N 2 o 3 [M+H] + = 283.1077, found 283.1098.

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Abstract

The invention provides a preparation method of multifunctional group-substituted imidazole derivatives including derivatives of 2,4,5-trisubstituted imidazole and 2-amino-4,5-disubstituted imidazole, and the derivatives are generated by alkenyl nitrine derivatives which are easy to be synthesized chemically and leaving group-containing imine compounds under a heating condition. The preparation method provided by the invention is reasonable in design, and easily available in raw materials, needs no addition of any auxiliary additive, and is simple and convenient in operation. The polysubstituted imidazole derivatives are as shown in general formula I in the description.

Description

Technical field [0001] The present invention is synthesized by compounds, mainly involving a preparation method of multi -alidine derivatives. Background technique [0002] Multi -replacement of mimazole derivatives have reportedly have good pharmaceutical properties and important physiological activity.Such a five-dollar heteroid derivative exists in hemoglobin oxidase -1-inhibitors, fatty acid amide hydrolytase inhibitors, γ-aminob-orblotic acid receptor agonists, etc.Mizazazole derivatives, especially the most replaced imidazole rings, have been reported in some listed drug structures, such as Rocastan and Simiidine.Therefore, this type of multi -replacement of mimazole derivatives is a very important type of five -yuan hybrid compound in pharmaceutical chemistry. [0003] There are many synthesis methods for multi -replacement of mimazole derivatives. Commonly built through UGI multi -components and Davidson ring combined methods, or start raw materials, such as amide, amine,...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C233/90C07D405/04
Inventor 罗婧陈文腾邵加安刘星雨俞永平
Owner ZHEJIANG UNIV
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