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Synthetic method of ethyl 2,4,6-triphenylnicotinate

A technique of triphenylnicotinic acid ethyl ester and a synthetic method, applied in the direction of organic chemistry, etc., can solve the problems of difficult substrates and cumbersome operations, and achieve the effects of easy-to-obtain, simple raw materials, and mild reaction conditions

Inactive Publication Date: 2019-12-27
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, these methods have some limitations, such as difficult access to substrates, cumbersome operation, use of expensive metal catalysts, high temperature and long-term reaction, etc.

Method used

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  • Synthetic method of ethyl 2,4,6-triphenylnicotinate
  • Synthetic method of ethyl 2,4,6-triphenylnicotinate

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] In a 10mL round bottom flask, add 0.24mmol (0.047g) (E)-1,3-diphenylpropene, 0.24mmol (0.054g) DDQ, 3mL1,4-dioxane, and stir at room temperature for 10 minutes , add 0.2mmol (0.038g) (E)-3-phenyl-3-aminoacrylic acid ethyl ester, react for 2 hours, then add 0.42mmol (0.095g) DDQ, continue to react for 0.5 hours, obtain the reaction solution and remove the solvent under reduced pressure , separated by column (200-300 mesh), using petroleum ether: ethyl acetate = 20:1 (volume ratio) as eluent, to obtain colorless oily ethyl 2,4,6-triphenylnicotinate ( 0.061g), the yield was 80%. 1 H NMR (500MHz, CDCl 3 ):8.19-8.17(m,2H),7.81-7.79(m,2H),7.77(s,1H),7.54-7.46(m,11H),4.02(q,J=7.1Hz,2H),0.93( t,J=7.1Hz,3H). 13 C NMR (125MHz, CDCl 3 ):168.7,157.2,156.6,149.6,140.0,138.6,138.5,129.5,128.7,128.6,128.5,128.2,128.1,127.2,126.8,119.4,61.3,13.4.ESI m / z[M+H] + 380.2.

Embodiment 2

[0025] In a 10mL round bottom flask, add 0.24mmol (0.047g) (E)-1,3-diphenylpropene, 0.2mmol (0.045g) DDQ, 3mL 1,4-dioxane, and stir at room temperature for 10 minutes Afterwards, add 0.2mmol (0.038g) (E)-3-phenyl-3-aminoacrylic acid ethyl ester, react for 2 hours, then add 0.4mmol (0.091g) DDQ, continue to react for 0.5 hours, and remove the reaction solution under reduced pressure Solvent, separated by column (200-300 mesh), using petroleum ether: ethyl acetate = 20:1 (volume ratio) as eluent, to obtain colorless oily ethyl 2,4,6-triphenylnicotinate (0.056 g), yield 74%.

Embodiment 3

[0027] In a 10mL round bottom flask, add 0.24mmol (0.047g) (E)-1,3-diphenylpropene, 0.24mmol (0.054g) DDQ, 4mL 1,4-dioxane, and stir at room temperature for 10 minutes After that, add 0.2mmol (0.038g) (E)-3-phenyl-3-aminoacrylic acid ethyl ester, react for 2 hours, then add 0.44mmol (0.10g) DDQ, continue to react for 0.5 hours, and remove the reaction solution under reduced pressure Solvent, separated by column (200-300 mesh), using petroleum ether: ethyl acetate = 20:1 (volume ratio) as eluent, to obtain colorless oily ethyl 2,4,6-triphenylnicotinate (0.055 g), yield 72%.

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Abstract

The invention discloses a synthetic method of ethyl 2,4,6-triphenylnicotinate. The method comprises the following steps of: reacting beta-enamine ester as shown in a formula I and 1,3-diphenyl propylene as shown in a formula II which are used as raw materials in an organic solvent, under the action of 1-1.2 equivalent of DDQ (2,3-dichloro-5,6-dicyano-1,4-benzoquinone) at room temperature for 2 h;adding 2.0-2.2 equivalent of DDQ, and continuing the reaction for 0.5 h to obtain a reaction solution; and carrying out post-treatment to obtain the ethyl 2,4,6-triphenylnicotinate represented by a formula III; wherein the mole ratio of the beta-enamine ester shown in the formula I, the 1,3-diphenyl propylene shown in the formula II, and the total DDQ is 1:(1-1.5):(3.0-3.4). According to the method, the reaction conditions are mild, a metal catalyst is not needed, the raw materials are simple and easy to obtain, the 2,3-dichloro-5,6-dicyano-1,4-benzoquinone is added in two times, the yield isas high as 80%, and a novel method is provided for synthesis of the ethyl 2,4,6-triphenylnicotinate.

Description

[0001] (1) Technical field [0002] The invention relates to a method for synthesizing ethyl 2,4,6-triphenylnicotinate. [0003] (2) Background technology [0004] Nicotinic acid ester is a natural product with various biological activities, and it is also an important structural unit of many pesticides and drugs. Therefore, it is of great significance to carry out the synthesis of nicotinic acid ester compounds. 2,4,6-Triphenylnicotinic acid ethyl ester is one of the nicotinic acid ester compounds. There are not many synthetic methods reported in the literature at present. There are mainly the following methods: The first method is the reaction of benzocyanide and Reformatsky reagent A β-enaminoester intermediate of zinc bromide is formed, which then undergoes a Michael addition reaction with an α,β-unsaturated ketone in the presence of indium trifluorosulfonate (Asian J.Org.Chem.2014,3 , 1108-1112); the second method is the series reaction of Rh(III) catalyzed N-sulfonyl-ket...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D213/80C07D213/803
CPCC07D213/80C07D213/803
Inventor 程冬萍邓志腾颜继忠
Owner ZHEJIANG UNIV OF TECH
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