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Synthesis method of pyridine-3-formate compound

A technology of ester compounds and synthesis methods, which is applied in the field of synthesis of pyridine-3-carboxylate compounds, can solve problems such as difficult availability of raw materials, low atom economy, cumbersome operation steps, etc., to avoid waste of resources and environmental pollution, Effect of high atom economy and simple synthesis process

Active Publication Date: 2018-02-27
HENAN NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

In view of its importance, people have successively developed some effective methods for constructing pyridine-3-carboxylate skeletons. Although most of these synthetic strategies are relatively effective, there are still some problems to be solved, such as: the raw materials are not easy to obtain, the reaction Harsh conditions, cumbersome operation steps, low atom economy, etc., so that its application in actual production is greatly limited

Method used

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  • Synthesis method of pyridine-3-formate compound
  • Synthesis method of pyridine-3-formate compound
  • Synthesis method of pyridine-3-formate compound

Examples

Experimental program
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Embodiment 1

[0016]

[0017] In a 15mL reaction tube, add propiophenone (1a, 0.6mmol, 80μL), ethyl 3-amino-3-phenylacrylate (2a, 0.5mmol, 95.6mg), Cu(OAc) 2 (0.05mmol, 9.1mg), 2,2'-bipyridine (bpy, 0.1mmol, 15.6mg), 2,2,6,6-tetramethylpiperidine nitrogen oxide (TEMPO, 0.5mmol, 78.1mg) and N,N-dimethylformamide (2 mL), the reaction tube was sealed in the presence of air, and then placed in an oil bath at 120° C. to stir for 20 h. After the reaction was completed, water was added to quench the reaction, extracted with ethyl acetate (8 mL×3), and then the organic phase was washed with water and saturated brine in sequence, and dried over anhydrous sodium sulfate. Filtered, spin-dried, and separated by silica gel column (petroleum ether / ethyl acetate=20 / 1) to obtain product 3a (115 mg, 76%) as a colorless liquid. The characterization data of this compound are as follows: 1 H NMR (600MHz, CDCl 3 )δ: 1.05(t, J=7.2Hz, 3H), 4.16(q, J=7.2Hz, 2H), 7.41-7.46(m, 6H), 7.64(d, J=6.6Hz, 2H), 7.72( ...

Embodiment 2

[0019] Add 1a (0.5mmol, 67μL), 2a (0.5mmol, 95.6mg), Cu(OAc) in sequence in a 15mL reaction tube 2 (0.05mmol, 9.1mg), 2,2'-bipyridine (0.1mmol, 15.6mg), 4-hydroxy-2,2,6,6-tetramethylpiperidine nitrogen oxide (4-HO-TEMPO, 0.5mmol, 86.1mg) and N,N-dimethylformamide (2mL), the reaction tube was sealed in the presence of air, then placed in an oil bath at 120°C and stirred for 20h. After the reaction was completed, water was added to quench the reaction, extracted with ethyl acetate (8 mL×3), and then the organic phase was washed with water and saturated brine in sequence, and dried over anhydrous sodium sulfate. Filtered, spin-dried, and separated by silica gel column (petroleum ether / ethyl acetate=20 / 1) to obtain product 3a (105 mg, 69%) as a colorless liquid.

Embodiment 3

[0021] Add 1a (1mmol, 133μL), 2a (0.5mmol, 95.6mg), Cu(OAc) in sequence in a 15mL reaction tube 2 (0.05mmol, 9.1mg), 2,2'-bipyridine (0.1mmol, 15.6mg), 4-hydroxy-2,2,6,6-tetramethylpiperidine nitrogen oxide (4-HO-TEMPO, 1.5mmol, 258.3mg) and N,N-dimethylformamide (2mL), the reaction tube was sealed in the presence of air, and then placed in an oil bath at 120°C and stirred for 20h. After the reaction was completed, water was added to quench the reaction, extracted with ethyl acetate (8 mL×3), and then the organic phase was washed with water and saturated brine in sequence, and dried over anhydrous sodium sulfate. Filtered, spin-dried, and separated by silica gel column (petroleum ether / ethyl acetate=20 / 1) to obtain product 3a (123 mg, 81%) as a colorless liquid.

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Abstract

The invention discloses a synthesis method of a pyridine-3-formate compound, and belongs to the technical field of organic synthesis. The synthesis method comprises the following step: using an aminoalkenoate compound and an alpha, beta-saturated ketone compound or an alpha, beta-saturated aldehyde compound as raw materials, and performing one-pot multi-step serial reaction under the action of acatalyst, a ligand and an oxidant to obtain the pyridine-3-formate compound. The synthesis method has the advantages of simple and convenient operation, mild conditions, wide application range of a substrate, and the like, and is suitable for industrial production.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a synthesis method of pyridine-3-carboxylate compounds. Background technique [0002] Pyridine-3-carboxylates are important nitrogen-containing heterocyclic compounds, and their main structural skeleton, pyridine, and pyridine derivatives are widely used in the synthesis of medicines, pesticides, spices, and chemicals. In addition, pyridine-3-carboxylates are important intermediates in organic synthesis. In view of its importance, people have successively developed some effective methods for constructing pyridine-3-carboxylate skeletons. Although most of these synthetic strategies are relatively effective, there are still some problems to be solved, such as: the raw materials are not easy to obtain, the reaction Harsh conditions, cumbersome operation steps, and low atom economy have greatly restricted its application in actual production. Therefore, it is ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D213/80C07D213/803C07D409/04C07B43/00
CPCC07B43/00C07D213/80C07D213/803C07D409/04
Inventor 范学森陈光张新迎王泽
Owner HENAN NORMAL UNIV
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