Preparation method of 1,2,3-bis-triazole ligands and application of 1,2,3-bis-triazole ligands in CuAAC reaction

Abstract

The invention discloses a preparation method of 1,2,3-bis-triazole ligands and an application of the 1,2,3-bis-triazole ligands in a CuAAC reaction. With cheap and easily available glycine methyl ester hydrochloride as a base raw material, and through derivation and conversion of functional groups, a diyne compound with glycine as a structure is obtained; then under a condition of room temperature and with organic azide as a raw material and copper iodide as a catalyst, 1,2,3-bis-triazole seven-membered-ring compounds are synthesized; and with the bis-triazole compounds and derivatives thereof as substrates, a series of methods for synthesis of the 1,2,3-bis-triazole derivatives are developed. A variety of novel, highly efficient, simple and easily available ligand catalysts are provided for a click reaction, and the 1,2,3-bis-triazole ligands have obvious effect on accelerating the reaction when used as the ligands and have quite practical application.

Description

technical field [0001] The invention belongs to the technical field of synthesis of functional structure molecules, and in particular relates to a preparation method of a 1,2,3-bistriazole ligand and its application in CuAAC reaction. Background technique [0002] Since the Sharpless and Medal working groups reported in 2002 that azide and terminal alkyne can generate a five-membered triazole ring (click reaction) under the catalysis of copper, the click reaction has developed very rapidly in all aspects of biochemistry. application. In order to improve the biocompatibility of the click reaction and reduce the toxic effect of Cu(I) on living cells, two important research areas of click chemistry work today: one is the copper-free catalyzed SPAAC reaction, and the other is the ability to react with monovalent copper Ligand compounds that coordinate ions and act as facilitators. The ligand has a very good effect on reducing the toxicity of copper ions to cells while accelera...

AI Technical Summary

Problems solved by technology

In recent years, although compounds with one-valent copper ligands have been reported one after another, the demand for ligand research and development is far from enough for the wide application of click reactions.

In the past, for the synthesis of such ligands, the synthesis conditions often required expensive reaction raw materials, it was difficult to synthesize in large quantities, and the reaction conditions were relatively harsh.

More importantly, when synthesizing such ligands, more expensive metal ligands are often required as catalysts to promote the synthesis of target ligand compounds. The reaction conditions are uneconomical and inconvenient for large-scale synthesis.

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