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Method for preparing polysubstituted tetrahydropyridine

A technology of tetrahydropyridine and multi-substitution, which is applied in the field of preparation of multi-substituted tetrahydropyridine, can solve the problems of non-conforming to green chemistry, impossibility of practical application, and many side reactions, and achieve economical steps, less pollution, and simple and easy operation Effect

Inactive Publication Date: 2012-08-15
NORTHWEST NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0006] Among these methods, some methods use organic solvents, and some methods require the use of heavy metal catalysts, low temperature and other conditions; in addition, some methods have many side reactions and low yields, which cannot be applied in practice and do not meet the requirements of green chemistry.

Method used

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  • Method for preparing polysubstituted tetrahydropyridine
  • Method for preparing polysubstituted tetrahydropyridine
  • Method for preparing polysubstituted tetrahydropyridine

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0021] Example 1, 1-(4-chlorophenyl)-4-(4-chloroanilino)-2,6-diphenyl-1,2,5,6-tetrahydropyridine-3-ethyl carbonate preparation

[0022] In the reaction flask (50mL round bottom flask) that has added ethanol (2mL), add benzaldehyde (0.212g, 2mmol), ethyl acetoacetate (0.260g, 2mmol), 4-chloroaniline (0.256g, 2mmol), Add 0.02mL of concentrated hydrochloric acid with a concentration of 12mol / L dropwise, and stir at 60°C for 23 hours at a controlled temperature; after the reaction, add ethyl acetate (15mL) and water (5mL) into the reaction flask, stir for 10 minutes, and then let it stand , liquid separation, the organic phase was separated, and the aqueous phase was extracted 3 times with ethyl acetate (10mL), and all the organic phases were combined, and the solvent was evaporated and recrystallized with ethanol-DMF (3 times), and finally the pure product 1 was obtained. -(4-Chlorophenyl)-4-(4-chloroanilino)-2,6-diphenyl-1,2,5,6-tetrahydropyridine-3-ethyl carbonate. Yield: 80%...

Embodiment 2

[0033] Example 2, 1-phenyl-4-anilino-2,6-bis(3,4-dimethoxyphenyl)-1,2,5,6-tetrahydropyridine-3-allyl carbonate Preparation of esters

[0034]In the reaction flask (50mL round bottom flask) that has added ethanol (2mL), add 3,4-dimethoxybenzaldehyde (0.332g, 2mmol), allyl acetoacetate (0.284g, 2mmol), aniline ( 0.186g, 2mmol), and then dropwise added 0.02mL of concentrated hydrochloric acid with a concentration of 12mol / L, controlled the temperature and stirred at 60°C for 19 hours; added ethyl acetate (15mL) and water (5mL ), stirred for 10 minutes and allowed to stand, separated the liquid, separated the organic phase, and extracted the aqueous phase with ethyl acetate (10mL) for 3 times, combined all the organic phases, evaporated the solvent and carried out recrystallization with ethanol-DMF (3 time), finally got the pure product 1-phenyl-4-anilino-2,6-bis(3,4-dimethoxyphenyl)-1,2,5,6-tetrahydropyridine-3-carbonic acid Allyl esters. Yield: 87%.

[0035] This product is ...

Embodiment 3

[0045] Example 3, 1-(4-chlorophenyl)-4-(4-chloroanilino)-2,6-bis(2-methoxyphenyl)-1,2,5,6-tetrahydropyridine - Preparation of 3-allyl carbonate

[0046] In the reaction flask (50mL round bottom flask) that has added ethanol (2mL), add 2-methoxybenzaldehyde (0.272g, 2mmol), allyl acetoacetate (0.284g, 2mmol), 4-chloroaniline ( 0.256g, 2mmol), then dropwise added 0.02mL of concentrated hydrochloric acid with a concentration of 12mol / L, controlled the temperature and stirred at 60°C for 19 hours; after the reaction was completed, ethyl acetate (15mL) and water (5mL) were added into the reaction flask, After stirring for 10 minutes, let it stand, separate the liquid, separate the organic phase, extract the aqueous phase with ethyl acetate (10mL) for 3 times, combine all the organic phases, evaporate the solvent and use ethanol-DMF for recrystallization (3 times) , finally get the pure product 1-(4-chlorophenyl)-4-(4-chloroanilino)-2,6-bis(2-methoxyphenyl)-1,2,5,6-tetrahydro Pyri...

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Abstract

The invention provides a new method for synthesizing polysubstituted tetrahydropyridine. In the method, a series of polysubstituted tetrahydropyridines are prepared by using low-cost and nontoxic hydrochloric acid as a catalyst and aromatic aldehyde, active methylene substances and aromatic amine as raw materials and by a one-pot process, the polysubstituted tetrahydropyridine yield (which is over 80 percent) is high; and the product quality (the purity is over 99 percent) is high; other organic solvents which are adverse to environment are not used in a reaction, so the pollution of the solvents and the catalyst on the environment is reduced, and the environmentally-friendly chemical synthesis is realized; and the polysubstituted tetrahydropyridine is synthesized by a multicomponent one-pot process, so the preparation method is economic in steps, simple in operation and low in cost, has mild reaction condition, is easy and convenient to operate, and is favorable for industrial production.

Description

technical field [0001] The invention belongs to the field of organic chemistry and relates to a method for preparing polysubstituted tetrahydropyridines, in particular to a method for preparing polysubstituted tetrahydropyridines by utilizing aromatic aldehydes, active methylene substances and aromatic amines. Background technique [0002] Multi-substituted tetrahydropyridines are an important class of organic compounds. Their structural skeletons exist in many natural products and molecules with biological activity. As the structural units of many biologically active compounds, they have attracted widespread attention. Multi-substituted tetrahydropyridine, its chemical structure is as follows: [0003] [0004] Among them, R 1 =H,4-CH 3 , 2-NO 2 , 3-NO 2 , 4-NO 2 , 2-Cl, 3-Cl, 4-Cl, 2, 4-DiCl, 2-OCH 3 , 4-OCH 3 ,3,4-DiOCH 3 ; 2 =CH 2 CH 3 , CH 2 CH=CH 2 ; 3 =H,4-CH 3 , 4-Cl, 4-Br. [0005] At present, there are many reports on the synthesis methods of pol...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D211/78
Inventor 王进贤高志荣周文俊
Owner NORTHWEST NORMAL UNIVERSITY
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