Method for synthesizing 4-phosphonic acid-1,5-substituted-1,2,3 triazole compounds through catalysis of ionic liquid

Abstract

The invention discloses a method for synthesizing 4-phosphonic acid-1,5-substituted-1,2,3 triazole compounds through catalysis of an ionic liquid and belongs to the technical field of synthesis of the triazole compounds. The technical scheme is characterized in that azide compounds and phosphorus ester compounds are taken as substrates, the ionic liquid is taken as a catalyst, methyl alcohol is taken as a solvent, the materials are subjected to stirring reaction at the temperature of 25-50 DEG C, and the 4-phosphonic acid-1,5-substituted-1,2,3 triazole compounds are prepared. The reaction time for the synthesis method is shorter, the reaction conditions are mild, the reaction temperature is 25-50 DEG C, the method requires no metal catalyst while a traditional click reaction requires transition metal as a catalyst, and accordingly, toxicity of metal ions is greatly reduced; phosphorylation is a method capable of improving properties of an index compound, with the introduction of a phosphoric acid group in drug design, the water solubility of the compound can be improved, so that bioavailability is improved, and part of prepared compounds have the fluorescence characteristic.

Description

technical field [0001] The invention belongs to the technical field of synthesis of triazole compounds, in particular to a method for catalyzing and synthesizing 4-phosphonic acid-1,5-substituted-1,2,3-triazole compounds by ionic liquids. Background technique [0002] In recent years, molecules containing 1,2,3-triazoles have been widely used in the design and synthesis of biologically active molecules, so a large number of synthetic methods for 1,4-substituted-1,2,3-triazoles have been reported , but the synthesis methods of 1,4,5-fully substituted-1,2,3-triazoles are still very limited, and 4-substituted-1,2,3-triazoles containing phosphonate groups are rare reports. In 2010, Muir et al. reported the use of 5-phosphonic acid-1,2,3-triazole as a stable phosphonic acid histidine analogue. First, the terminal alkyne compound was reacted with phosphite to obtain ethynylphosphine ester, and then selectively synthesize 5-phosphonic acid-1,2,3-triazole by Ru-catalyzed reaction ...

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Problems solved by technology

[0002] In recent years, molecules containing 1,2,3-triazoles have been widely used in the design and synthesis of biologically active molecules, so a large number of synthetic methods for 1,4-substituted-1,2,3-triazoles have been reported , but the synthesis methods of 1,4,5-fully substituted-1,2,3-triazoles are still very limited, and 4-substituted-1,2,3-triazoles containing phosphonate groups are rare to report

In 2010, Muir et al. reported the use of 5-phosphonic acid-1,2,3-triazole as a stable phosphonic acid histidine analogue. First, the terminal alkyne compound was reacted with phosphite to obtain ethynylphosphine ester, and then selectively synthesize 5-phosphonic acid-1,2,3-triazole by Ru-catalyzed reaction of alkynyl phosphonate with azide, which requires the use of strong base nBuLi to synthesize ethynylphosphine ester, and using this method to synthesize 5-phosphonic acid-1,2,3-triazole can not introduce any substituents at the 4-position, which limits the further expansion of the substrate

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