Method for synthesizing (E)-2-methyl-4-phenyl-6-styryl-substitued pyridine compound

A styryl-based, synthetic method technology, applied in organic chemistry methods, organic chemistry and other directions, can solve the problems of harsh conditions, high cost, expensive, etc., and achieve the effects of fewer experimental steps, low technical difficulty, and mild conditions

Inactive Publication Date: 2018-05-18
HENAN NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

There are more or less many defects in the traditional methods or processes, such as: (1) the use of expensive metal-organic reagents, special phosphine ligands, etc., which is costly and unfavorable for industrial production; (2) requires high temperature, multiple One-step reaction, the conditions are harsh, which limits the practical application of the reaction; (3) the yield and selectivity are still not high enough, and need to be further improved, etc.

Method used

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  • Method for synthesizing (E)-2-methyl-4-phenyl-6-styryl-substitued pyridine compound
  • Method for synthesizing (E)-2-methyl-4-phenyl-6-styryl-substitued pyridine compound
  • Method for synthesizing (E)-2-methyl-4-phenyl-6-styryl-substitued pyridine compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] Example 1: (E)-2-methyl-4-phenyl-6-styrylpyridine 2a

[0038]

[0039] Under nitrogen atmosphere, 0.6mmol (2E,3E)-4-phenylbut-3-en-2-one-O-acetyl oxime compound 1a, 0.9mmol sodium bisulfite, 0.03mmol cuprous bromide and 2 mL of 1,4-dioxane was sequentially added into the Schlenk reaction tube, heated to 100° C. and stirred for 12 h in IKA. After the reaction, cool to room temperature, transfer the reaction liquid with 20 mL of ethyl acetate, prepare a sample by rotary evaporation under reduced pressure, and separate by column chromatography to obtain the target product 2a (68%). The characterization data of this compound are as follows: 1 H NMR (600MHz, CDCl 3 ):7.65(dd, J=12.0,6.0Hz,3H),7.60(d,J=6.0Hz,2H),7.49(t,J=9.0Hz,2H),7.43(t,J=6.0Hz,2H ), 7.37(t, J=6.0Hz, 2H), 7.29(t, J=6.0Hz, 1H), 7.24(dd, J=12.0, 6.0Hz, 2H), 2.65(s, 3H); 13 C NMR (101MHz, CDCl 3 ): 158.8, 155.7, 149.3, 138.7, 136.8, 132.6, 129.0, 128.9, 128.7, 128.5, 128.2, 127.1, 127.1, 119.9, 117.2, 2...

Embodiment 2

[0040] Example 2: (E)-2-methyl-6-(4-methylstyryl)-4-p-tolylpyridine 2b

[0041]

[0042]Under nitrogen atmosphere, 0.6mmol (2E,3E)-4-phenylbut-3-en-2-one-O-acetyl oxime compound 1b, 0.9mmol sodium bisulfite, 0.03mmol cuprous bromide and 2 mL of 1,4-dioxane was sequentially added into the Schlenk reaction tube, heated to 100° C. and stirred for 12 h in IKA. After the reaction, cool to room temperature, transfer the reaction liquid with 20 mL of ethyl acetate, prepare a sample by rotary evaporation under reduced pressure, and separate by column chromatography to obtain the target product 2b (59%).

Embodiment 3

[0043] Example 3: (E)-4-(4-methoxyphenyl)-2-(4-methoxystyryl)-6-methylpyridine 2c

[0044]

[0045] Under nitrogen atmosphere, 0.6mmol (2E,3E)-4-phenylbut-3-en-2-one-O-acetyl oxime compound 1c, 0.9mmol sodium bisulfite, 0.03mmol cuprous bromide and 2 mL of 1,4-dioxane was sequentially added into the Schlenk reaction tube, heated to 100° C. and stirred for 12 h in IKA. After the reaction, cool to room temperature, transfer the reaction liquid with 20 mL of ethyl acetate, prepare a sample by rotary evaporation under reduced pressure, and separate by column chromatography to obtain the target product 2c (63%). The characterization data of this compound are as follows: 1 H NMR (400MHz, CDCl 3 ):7.63-7.53(m,5H),7.39(s,1H),7.18-7.08(m,2H),7.02-7.00(m,2H),6.91(d,J=8.0Hz,2H),3.87( s,3H),3.84(s,3H),2.63(s,3H); 13 C NMR (151MHz, CDCl 3 ): 160.4, 159.8, 158.5, 155.9, 148.7, 132.1, 131.0, 130.5, 129.6, 128.4, 128.2, 128.0, 126.4, 119.0, 116.4, 114.4, 114.3, 114.2, 113.7, 55.2, 45....

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Abstract

The invention discloses a method for synthesizing (E)-2-methyl-4-phenyl-6-styryl-substitued pyridine compound, and belongs to the technical field of organic chemistry. (2E, 3E)-4-phenylbutyl-3-ene-2-one-O-acetyloxime compound is taken as a raw material, in the presence of sodium bisulfite and cuprous bromide, the compound is heated in a reaction solvent, and a reaction is carried out to obtain the(E)-2-methyl-4-phenyl-6-styryl-substitued pyridine compound. Bimolecular (2E, 3E)-4-phenylbutyl-3-ene-2-one-O-acetyloxime is used to establish a functional multi-substituted pyridine compound via a one-step reaction. The method is high in reaction yield, and the substrate adapts to a wide application range.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a method for synthesizing (E)-2-methyl-4-phenyl-6-styryl substituted pyridine compounds. Background technique [0002] As an important nitrogen-containing heterocycle, pyridine exists in a variety of important compounds, including azine, vitamin niacin, and pyridoxine. It is not only the precursor of chemicals and drugs, but also an important dye assistant and denaturant. Pyridine derivatives are the parent or fragment structures of many compounds, which constitute an important part of natural products, functional materials, and medicinal chemistry. It is precisely because of its potential application prospects in various fields that it has attracted the attention and attention of scientists, and a lot of research has been done on it, and many valuable scientific research results have been obtained. [0003] The synthesis of pyridine derivatives, especiall...

Claims

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Application Information

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IPC IPC(8): C07D213/06C07D213/30C07D213/08C07D409/14C07D213/26C07D405/14
CPCC07B2200/09C07D213/06C07D213/08C07D213/26C07D213/30C07D405/14C07D409/14
Inventor刘建明岳园园赵淑芳闫旭洋王智贤王智玥
OwnerHENAN NORMAL UNIV