Method for synthesizing pyrazine derivatives through intermolecular [3+3] dimerization of chiral imines

An intermolecular and pyrazine technology, which is used in the field of [3+3] dimerization of chiral imines to form pyrazine derivatives, can solve the problem of many side reactions, difficult to improve product yield, and increase the difficulty of processing and other problems, to achieve the effect of high yield, mild reaction conditions and simple treatment process

Active Publication Date: 2019-08-16
SOUTHWEST FORESTRY UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0009] At present, the main problems of the widely used traditional synthesis methods are: 1. The conditions of some reaction equipment are special, such as dehydration, dehydrogenation, and deamination reactions. There are higher requirements for high temperature resistance and high pressure resistance
3. Many reaction routes use strong acid and strong base. The introduction of strong acid and strong base reaction conditions will increase the difficulty of post-reaction treatment and cause more environmental problems
4. There are many side reactions, and it is difficult to increase the product yield, etc.

Method used

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  • Method for synthesizing pyrazine derivatives through intermolecular [3+3] dimerization of chiral imines
  • Method for synthesizing pyrazine derivatives through intermolecular [3+3] dimerization of chiral imines
  • Method for synthesizing pyrazine derivatives through intermolecular [3+3] dimerization of chiral imines

Examples

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Effect test

Embodiment 1

[0038] This example provides a method for the intermolecular [3+3] dimerization of chiral imines into pyrazine derivatives. Using cinnamaldehyde and chiral tert-butylsulfinamide as raw materials, under the action of a catalyst, synthesize Chiral imine compounds, and then synthesize pyrazine derivatives 2,5-dimethyl((z)-benzoaldehyde)-2,5-dihydropyrazine through dimerization reaction under the action of alkaline substances ; Its synthetic route is as follows:

[0039]

[0040] This embodiment provides a method for intermolecular [3+3] dimerization of chiral imines to form pyrazine derivatives, including the following steps:

[0041] (1) Using cinnamaldehyde containing α,β-unsaturated conjugated aldehyde structure and chiral tert-butyl sulfinamide, under the action of Lewis acid tetraethyl titanate, it is formed by dehydration and condensation of aldehyde group and amine group Chiral conjugated imine compounds,

[0042] (2) adding under the effect of inorganic alkali cesium...

Embodiment 2

[0050] This example provides a method for the intermolecular [3+3] dimerization of chiral imines into pyrazine derivatives. Using cinnamaldehyde and chiral tert-butylsulfinamide as raw materials, under the action of a catalyst, synthesize Chiral imine compounds, and then synthesize pyrazine derivatives 2,5-dimethyl((z)-benzoaldehyde)-2,5-dihydropyrazine through dimerization reaction under the action of alkaline substances ; Its synthetic route is as follows:

[0051]

[0052] This example provides a method for intermolecular [3+3] dimerization of chiral imines into pyrazine derivatives, including the following steps:

[0053] (1) Using cinnamaldehyde containing α,β-unsaturated conjugated aldehyde structure and chiral tert-butyl sulfinamide, under the action of Lewis acid tetraethyl titanate, it is formed by dehydration and condensation of aldehyde group and amine group Chiral conjugated imine compounds,

[0054] (2) adding under the effect of inorganic alkali cesium carbo...

Embodiment 3

[0062] This example provides a method for intermolecular [3+3] dimerization of chiral imines into pyrazine derivatives: using cinnamaldehyde (1.74g, 13.20mmol), (R)-tert-butylsulfinamide (1.45g, 12.00mmol), tetraethyl titanate (Ti(EtO) 4 , 5mL, 24.00mmol), add dry tetrahydrofuran (20mL) and a round-bottomed flask with a magnetic stirrer, heat at 50°C under the protection of an inert gas, and the reaction time is 4 hours. ) to monitor the progress of the reaction.

[0063] Post-reaction processing:

[0064] Monitor the complete disappearance of the reaction raw material cinnamaldehyde by TLC, stop heating, add saturated sodium bicarbonate solution under rapid and vigorous stirring after cooling to room temperature until a white precipitate appears, filter and wash the filter cake with ethyl acetate, and pass the filtrate through saturated sodium chloride solution After washing and extraction with ethyl acetate, the organic solvent phase is collected, dried over anhydrous magn...

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Abstract

The invention discloses a method for synthesizing pyrazine derivatives through intermolecular [3+3] dimerization of chiral imines, which is characterized in that cinnamyl aldehyde and chiral tert-butyl sulfinamide are taken as raw materials to synthesize chiral imine compounds, and then dimerization reaction is carried out to synthesize the pyrazine derivatives. The synthetic route of the method is shown in the specification. According to the method, the tert-butyl sulfinamide is used for induction so as to remove free radicals under the heating condition, and the target product can be obtained only by adding Cs2CO3 weak alkali in the reaction process, so that the special requirements of strong conditions on a reaction device can be avoided. The method is mild and rapid in reaction condition and high in yield, and the obtained product is of a symmetrical structure. The invention provides a new idea for synthesis of symmetrical dimer molecules, the reaction post-treatment process is simple, and reaction raw materials can be converted into a single product due to high efficiency of the reactions.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a method for [3+3] dimerization of chiral imine molecules into pyrazine derivatives. Background technique [0002] Pyrazine is a key part of the molecular structure of many drugs, such as norfloxacin, pipemidic acid, pyrazine salts (phosphate, sulfate), quinolones, rifampicin, etc. Many pyrazines and their derivatives have important biological activities, such as antibacterial, anti-inflammatory, hypoglycemic and other activities. Pyrazine compounds have aroused great interest of organic synthetic chemists and medicinal chemists as early as the 19th century, and modern drug research has devoted a lot of energy to the expansion, development and application of pyrazine compounds. [0003] For the synthesis of pyrazine compounds, according to different raw materials can be roughly divided into the following categories: [0004] 1. Synthesize with monoethanola...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D241/12
CPCC07D241/12C07B2200/09
Inventor 周备杜官本胡敏陶云凤和宇娟谢格格张金成
Owner SOUTHWEST FORESTRY UNIVERSITY
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