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Method for preparing polyhydroquinolines

A polyhydroquinoline and hydroquinoline technology, applied in the field of organic chemical synthesis, can solve the problems of expensive catalysts, incompatible with green chemistry, and unfavorable industrial production, and achieve the goals of simplified post-processing, high yield, and reduced pollution Effect

Inactive Publication Date: 2012-07-04
NORTHWEST NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

All these methods have problems such as the use of expensive catalysts, a large amount of organic solvents, long reaction times, complicated post-treatment, and low yields, especially the catalytic reaction causes greater pollution to the environment, does not meet the requirements of green chemistry, and is not conducive to industrial production

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  • Method for preparing polyhydroquinolines
  • Method for preparing polyhydroquinolines
  • Method for preparing polyhydroquinolines

Examples

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Effect test

Embodiment 1

[0018] Example 1, Preparation of 2-methyl-4-(2-thienyl)-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylic acid ethyl ester

[0019] Filled with 0.30g PEG-400-H 2 O (PEG-400 0.15g, H 2 O 0.15g) into the reaction flask (50 mL round bottom flask) of the mixed solution, add 1mmol of thiophenealdehyde, 1mmol of 1,3-cyclohexanedione, 1mmol of ethyl acetoacetate, and 1.5mmol of ammonium acetate in sequence, and stir at 90°C React for 3 minutes; after the reaction, cool the reaction bottle to room temperature, add 6 mL of distilled water, and wash the reaction mixture twice; heat to dissolve with absolute ethanol, and recrystallize 4-5 times to obtain pure 2-methyl-4-(2 Preparation of -thienyl)-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylic acid ethyl ester.

[0020] This product is a yellow solid with a melting point of 251-253°C and a yield of 94%.

[0021] The infrared spectrum data of product of the present invention is as follows:

[0022] IR (υ / cm -1 ):3289, 3213, 30...

Embodiment 2

[0031] Example 2, 2-methyl-4-(5-methyl-2-furyl)-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylic acid ethyl Preparation of esters

[0032] Filled with 0.30g PEG-400-H 2 O (PEG-400 0.15g, H 2 O 0.15g) into the reaction flask (50 mL round bottom flask) of the mixed solution, add 1mmol of 5-methyl-2 furanal, 1mmol of 1,3-cyclohexanedione, 1mmol of ethyl acetoacetate, and 1.8mmol of ammonium acetate , stirred and reacted at 80°C for 5 minutes; after the reaction, cooled the reaction bottle to room temperature, added 6 mL of distilled water, and washed the reaction mixture twice; heated and dissolved with absolute ethanol, and recrystallized 4-5 times to obtain pure 2-formazan Preparation of ethyl 4-(5-methyl-2-furyl)-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate.

[0033] This product is a yellow solid with a melting point of 239-241°C and a yield of 88%.

[0034] The infrared spectrum data of product of the present invention is as follows:

[0035] IR (υ / cm -1 ): 3291...

Embodiment 3

[0044] Example 3, 2-methyl-4-(3-ethoxy-4-hydroxyphenyl)-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxyl Preparation of ethyl acetate

[0045] Filled with 0.30g PEG-400-H 2 O (PEG-400 0.15g, H 2 O 0.15g) into the reaction flask (50 mL round bottom flask) of the mixed solution, add 1 mmol of 4-hydroxy-3 ethoxybenzaldehyde, 1 mmol of 1,3-cyclohexanedione, 1 mmol of ethyl acetoacetate, ammonium acetate 2mmol, stirred and reacted at 70°C for 8 minutes; after the reaction, cooled the reaction bottle to room temperature, added 6mL of distilled water, and washed the reaction mixture twice; heated and dissolved with absolute ethanol, and recrystallized 4-5 times to obtain the pure product 2- Preparation of ethyl methyl-4-(3-ethoxy-4-hydroxyphenyl)-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate.

[0046] This product is a light yellow solid with a melting point of 213-214°C. Yield: 98%.

[0047] The infrared spectrum data of product of the present invention is as follows:

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Abstract

The invention provides a method for synthesizing polyhydroquinolines in the absence of a catalyst, which is to synthesize polyhydroquinolines by one-pot reaction of an aromatic aldehyde, 1,3-cyclohexanedione, ethyl acetoacetate and ammonium acetate in a PEG-400-H2O system. The method avoids using any catalyst, thereby reducing environmental pollution caused by catalysts, simplifying post treatment process and realizing environmentally-friendly synthesis; the method makes process simple and operation convenient; and the method realizes mild reaction conditions, short reaction time and high yield (over 80 percent), and contributes to industrial production.

Description

technical field [0001] The invention belongs to the technical field of organic chemical synthesis, and relates to a preparation method of polyhydroquinoline, in particular to a method for preparing polyhydroquinoline under non-catalytic conditions. Background technique [0002] In addition to having a wide range of bactericidal and anti-inflammatory biological activities, polyhydroquinoline compounds are also used in antimalarial agents and clinically as drugs for the treatment of cardiovascular diseases, such as calcium channel blockers for the treatment of cardiovascular diseases, anti Hypertensive drugs, etc., have therefore received widespread attention. 1, polyhydroquinoline compound, its chemical structural formula is as follows: [0003] [0004] Where, R = 2-Thienyl, 5-Methyl-2-furyl, 4-OH-3-C 2 h 5 OC 6 h 3 , 2-CH 3 OC 6 h 4 . [0005] At present, there are many reports on the synthetic methods of polyhydroquinolines. Among them, the catalytic reaction ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D409/04C07D405/04C07D215/54
Inventor 王进贤孙永军
Owner NORTHWEST NORMAL UNIVERSITY
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