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Synthetic method of bicyclic pyridone derivative

A technique for the synthesis of bicyclic pyridone and its synthesis method, which is applied in the field of synthesizing bicyclic pyridone derivatives, can solve the problems of limiting the application of bicyclic pyridone derivatives, molecular structure restrictions, etc., and achieve high product yield, simple operation, and easy reaction. The effect of mild conditions

Inactive Publication Date: 2012-12-26
DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, limited by the molecular structure of the raw material, the molecular structure of the bicyclic pyridone derivatives that can be synthesized by the above method is also limited, thus limiting the application of the synthetic bicyclic pyridone derivatives

Method used

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  • Synthetic method of bicyclic pyridone derivative
  • Synthetic method of bicyclic pyridone derivative
  • Synthetic method of bicyclic pyridone derivative

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029]

[0030] In a 25mL Schlenk reaction flask, add 5,5-dialkylthio-2,4-pentadienoate 2a (65mg, 0.25mmol), organic diprimary amine 1,2-ethylenediamine (3a) ( 18mg, 0.30mmol) and 2mL solvent ethanol, stirred and refluxed for 14h. After the reaction, the mixture was cooled to room temperature, the volatile components were removed under reduced pressure, and then separated by silica gel column chromatography, the eluent was petroleum ether (60-90°C) / acetone, (v / v=3:1) , to obtain the target product 1a (35 mg, yield 79%) as a white solid. The target product was confirmed by NMR and high-resolution mass spectrometry.

Embodiment 2

[0032] The reaction steps and operations are the same as in Example 1, except that the reaction time is 24 hours. The reaction was stopped, and the target product 1a (32 mg, yield 72%) was obtained after post-processing. It shows that prolonging the reaction time leads to partial decomposition of the product.

Embodiment 3

[0034] The reaction steps and operations are the same as in Example 1, except that the reaction temperature is room temperature 20° C. and the reaction time is 24 hours. The reaction was stopped, and the target product 1a (8 mg, yield 17%) was obtained after post-processing. It shows that the reaction temperature is too low to slow down the reaction.

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Abstract

The invention discloses a method for synthesizing a bicyclic pyridone derivative with potential bioactivity, comprising the following steps that: 5,5-bisalkylthio-2,4-pentadienoic acid ester used as a raw material with the characteristics of being easy to prepare, having structural diversity and multiple reactive centers and a bimolecular nucleophilic reagent organic diprimary amine is subject to substitution / condensation in refluxing to synthesize the bicyclic pyridone derivative. Compared with the reported synthetic methods of the bicyclic pyridone derivative, the method disclosed in the invention has the advantages of being convenient for raw materials, simple operation, mild reaction conditions and high efficiency.

Description

technical field [0001] The present invention relates to a method for synthesizing bicyclic pyridone derivatives. The 5,5-dialkylthio-2,4-pentadienoic acid ester, which is easy to prepare, has structural diversity and multiple reaction centers, is used as a raw material to perform a substitution / condensation reaction with a dinucleophile organic diprimary amine to obtain a bicyclic Pyridone derivatives. Compared with the reported synthesis method of bicyclic pyridone derivatives, the present invention has easy-to-obtain raw materials, simple and convenient operation, mild synthesis reaction conditions and high efficiency. Background technique [0002] Bicyclic pyridone derivatives are an important class of potentially biologically active N-heterocyclic compounds, and they have received widespread attention as potential analgesic and anti-inflammatory drugs. The 2003 Bayer patent (WO2003053967A1) and the 2005 Amgen patent (WO2005 / 070932A2) reported that through the regulatio...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D471/04
Inventor 余正坤于海丰
Owner DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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