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Functionalized ionic liquid ligand used for CuAAC reaction, and preparation method and applications thereof

An ionic liquid and functionalization technology, applied in chemical instruments and methods, organic compound/hydride/coordination complex catalysts, organic chemistry, etc., can solve the problems that functionalized ionic liquid ligands have not been reported, and achieve high efficiency The effect of promoting CuAAC reaction in water phase, good water solubility and excellent performance

Active Publication Date: 2018-10-09
HENAN NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, at present, people use alkyne-functionalized ionic liquids for further functional design, and the preparation of functionalized ionic liquid ligands has not been reported.

Method used

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  • Functionalized ionic liquid ligand used for CuAAC reaction, and preparation method and applications thereof
  • Functionalized ionic liquid ligand used for CuAAC reaction, and preparation method and applications thereof
  • Functionalized ionic liquid ligand used for CuAAC reaction, and preparation method and applications thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0021] In a 25mL round-bottomed flask, add 2mmol of tripropargylamine, 8mmol of 1-azido-3-chloropropane, 0.4mmol of cuprous iodide, 10mL of acetonitrile and 4mmol of DIPEA, seal it with a rubber stopper, and stir at room temperature for 24 hours , filtered after the reaction was completed, the solvent and DIPEA were removed by rotary evaporation under reduced pressure, and the pure chloro-click product was obtained by silica gel column chromatography, and the separation yield was 86%.

Embodiment 2

[0023] In a 25mL round-bottomed flask, add 1mmol of the chloro-click product, 6mmol of sodium azide and 10mL of DMF successively, filter after the reaction, remove the DMF by rotary evaporation under reduced pressure, and obtain the pure azide-based click product by silica gel column chromatography. Yield 95%.

Embodiment 3

[0025]

[0026]

[0027] Add 0.5mmol of azide-based click product, 1.5mmol of imidazolynyl functionalized ionic liquid, 0.2mmol of cuprous iodide, 5mL of acetonitrile and 2mmol of DIPEA in a 25mL round-bottomed flask, seal with a rubber stopper, and stir at 60°C for 24 Hours, after the reaction was completed, it was filtered, and the solvent and DIPEA were removed by rotary evaporation under reduced pressure, extracted with ether and water, the water phase was filtered again, rotary evaporated under reduced pressure, and then vacuum-dried at 60°C to obtain the functionalized imidazole ionic liquid ligand L1.

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Abstract

The invention discloses a functionalized ionic liquid ligand used for CuAAC reaction, and a preparation method and applications thereof, and belongs to the technical field of functionalized ionic liquid ligand synthesis and CuAAC reaction. The technical scheme main points are that: an alkynyl functionalized ionic liquid is taken as a precursor, clinck reaction is adopted for further functionalization design so as to obtain the novel functionalized ionic liquid ligand. The functionalized ionic liquid ligand is capable of promoting CuAAC reaction in water phase preferably. Compared with TBTA ligand in the prior art, the advantages are that: the functionalized ionic liquid ligand is excellent in water solubility, is capable of promoting water phase CuAAC reaction with high efficiency, and great advantages are achieved in applications of the functionalized ionic liquid ligand in chemical production and medicine synthesis using water phase CuAAC reaction.

Description

technical field [0001] The invention belongs to the technical field of synthesis of functionalized ionic liquid ligands and CuAAC reaction, and in particular relates to a class of functionalized ionic liquid ligands for CuAAC reaction and its preparation method and application. Background technique [0002] Click chemistry plays an important role in the field of molecular design and synthesis. The Cu-catalyzed click reaction of alkyne and azide (CuAAC reaction) can be carried out efficiently under mild conditions, so it has received extensive attention (Wang K, BiX, Xing S, et al. Cu 2 O acting as a robust catalyst in CuAAC reactions: water is the required medium [J]. Green Chemistry, 2011, 13(3): 562-565.). The general CuAAC reaction model includes alkynes, azides, suitable solvents, ligands or bases. With the deepening of related research, people began to seek more advantageous click reaction models, including less Cu dosage, faster reaction rate, better biocompatibility...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D403/14C07D249/04B01J31/02C07D405/04
CPCB01J31/0279B01J31/0284C07D249/04C07D403/14C07D405/04
Inventor 朱安莲李凌君唐明洁李启星
Owner HENAN NORMAL UNIV
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