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2,3,5,6-tetrasubstituted-3H-1,2,4-triazine derivative and synthesis method thereof

A technology for triazine derivatives and synthesis methods, applied in the direction of organic chemistry and the like, can solve the problems of harsh reaction conditions, limited types of substrates, poor regioselectivity, etc., and achieve the effects of low cost, cost advantage, and good functional group diversity.

Inactive Publication Date: 2019-10-22
NANJING NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, most of the synthetic methods have problems such as limited substrate types, cumbersome preparation, harsh reaction conditions, and poor regioselectivity.

Method used

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  • 2,3,5,6-tetrasubstituted-3H-1,2,4-triazine derivative and synthesis method thereof
  • 2,3,5,6-tetrasubstituted-3H-1,2,4-triazine derivative and synthesis method thereof
  • 2,3,5,6-tetrasubstituted-3H-1,2,4-triazine derivative and synthesis method thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040]

[0041] Weigh successively α-carbonyl enamine 2a (0.5mmol), boron tetrafluoride benzene diazonium salt 3a (0.6mmol), copper bromide (0.05mmol), potassium phosphate (2.0mmol) in a 25mL Schlenk reaction flask, in Under air, 5 mL of DMSO solvent was added, stirred at room temperature for 2 minutes, and reacted in an oil bath at 60° C. for 1.2 hours. After the reaction, the mixture was cooled to room temperature, filtered with diatomaceous earth, extracted with ethyl acetate and 10% ammonia water in mass concentration, collected the organic phase, dried over anhydrous magnesium sulfate, filtered, removed volatile components under reduced pressure, and then used a silica gel column to Chromatographic separation (eluent: petroleum ether (60-90°C) / ethyl acetate, v / v=10:1) gave the target product 1aa (159 mg, yield 90%) as a yellow liquid. The target product was confirmed by NMR and high-resolution mass spectrometry.

Embodiment 2

[0043]

[0044]Sequentially weigh α-carbonyl enamine 2a (0.5mmol), boron tetrafluoride p-bromobenzenediazonium salt 3b (0.6mmol), copper chloride (0.15mmol), potassium carbonate (1.5mmol) in a 25mL Schlenk reaction flask , under the air, add DMF solvent 5mL, stir at room temperature for 2 minutes, put into 80°C oil bath to react for 1.2 hours. After the reaction, the mixture was cooled to room temperature, filtered with diatomaceous earth, extracted with ethyl acetate and 10% ammonia water in mass concentration, collected the organic phase, dried over anhydrous magnesium sulfate, filtered, removed volatile components under reduced pressure, and then used a silica gel column to Chromatographic separation (eluent: petroleum ether (60-90°C) / ethyl acetate, v / v=10:1) gave the target product 1ab (140 mg, yield 65%) as a yellow liquid. The target product was confirmed by NMR and high-resolution mass spectrometry.

Embodiment 3

[0046]

[0047] Weigh successively α-carbonyl enamine 2a (0.5mmol), boron tetrafluoride p-chlorobenzene diazonium salt 3c (0.6mmol), copper acetate (0.1mmol), cesium carbonate (1.0mmol) in a 25mL Schlenk reaction flask, Under argon, 5 mL of DMF / DMSO mixed solvent was added, stirred at room temperature for 2 minutes, and reacted in an oil bath at 60° C. for 2.0 hours. After the reaction, the mixture was cooled to room temperature, filtered with diatomaceous earth, extracted with ethyl acetate and 10% ammonia water in mass concentration, collected the organic phase, dried over anhydrous magnesium sulfate, filtered, removed volatile components under reduced pressure, and then used a silica gel column to Chromatographic separation (eluent: petroleum ether (60-90°C) / ethyl acetate, v / v=10:1) gave the target product 1ac (130 mg, yield 67%) as a yellow liquid. The target product was confirmed by NMR and high-resolution mass spectrometry.

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Abstract

The invention discloses a 2,3,5,6-tetrasubstituted-3H-1,2,4-triazine derivative and a synthesis method thereof. Alpha-carbonylenamine and a diazonium salt are taken as starting materials for constructing two C-N bonds in one the step through substitution and cyclization reaction under alkaline conditions in the presence of a copper salt as a catalyst to generate the 2,3,5,6-tetrasubstituted-3H-1,2,4-triazine derivative, and the obtained triazine derivatives have certain potential drug activity. The method has the advantages of easily available raw materials, simple and convenient operation, mild synthesis reaction conditions, high reaction efficiency and diversity of functional groups.

Description

technical field [0001] The invention belongs to chemical synthesis technology, in particular to an unsaturated nitrogen-containing heterocyclic compound 2,3,5,6-tetrasubstituted-3H-1,2,4-triazine derivative and a synthesis method thereof. Background technique [0002] Nitrogen heterocyclic compounds are an important branch of heterocyclic compounds, which are ubiquitous in nature, widely present in natural products and bioactive molecules, and have important uses in the fields of medicine and material chemistry. 1,2,4-Triazine is an important class of nitrogen heterocyclic compounds, often used as metal ligands and fluorescent probes (J.Chem.Sci.2015,6,4812), and can also be used as hetero-Diels-Alder Intermediates of cycloaddition reactions, construct various nitrogen heterocyclic derivatives (J.Am.Chem.Soc.2015,137,8388), and have various biological activities such as anticancer, antidiabetic, antifungal, anti Epilepsy, antimalarial (Bioorg.Med.Chem.2007, 15, 343), etc., ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D253/06C07D405/04
CPCC07D253/06C07D405/04
Inventor 黄菲丁奇峰于杨杨雅琼李明瑞黄和乔纳森贝尔
Owner NANJING NORMAL UNIVERSITY
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