Preparation method of N-vinyl-1,2,3-triazole compound

A compound, vinyl technology, applied in the field of preparation of N-vinyl-1,2,3-triazole compounds, can solve problems such as damage, achieve easy separation and purification, excellent substrate universality, good Yield effect

Active Publication Date: 2019-03-22
SHANDONG NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At the same time, these mentioned limitations impair the important role of vinyl-1,2,3-triazoles in medicinal chemistry, since the pharmaceutical properties of triazoles are closely related to the type of substitution

Method used

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  • Preparation method of N-vinyl-1,2,3-triazole compound
  • Preparation method of N-vinyl-1,2,3-triazole compound

Examples

Experimental program
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Effect test

Embodiment 1

[0053] A preparation method of N-vinyl-1,2,3-triazole compounds, the reaction process is as shown in formula (3):

[0054]

[0055] The reaction specifically includes the following steps:

[0056] (1) Compound 1a, namely phenylacetylene (34uL, 0.3mmol), compound 2 (82mg, 0.2mmol), NaBH 4 (3.8mg, 0.4mmol), join in 1mL acetonitrile and 1mL triethylamine, then add catalyst Pd(PPh 3 ) 4 (4.7mg, 0.004mmol) and CuI (1.5mg, 0.008mmol), under argon protection, heated and stirred at 60°C for 4h, TLC detected that the substrate disappeared, and the reaction was over; the liquid;

[0057] (2) the viscous liquid obtained in step (1) is subjected to silica gel column chromatography (eluent is V 石油醚 :V 乙酸乙酯 =5:1) to obtain compound 3a with a yield as high as 91%.

[0058] Compound 3a prepared in the present embodiment 1 H-NMR and 13 The nuclear magnetic resonance spectra of C NMR are as follows figure 1 and 2 As shown, the result is:

[0059] 1 H NMR (400MHz, CDCl 3 )δ8.00(s...

Embodiment 2

[0066] A preparation method of N-vinyl-1,2,3-triazole compounds, the reaction process is as formula (3) in Example 1; the difference is:

[0067] (1) Compound 1a is phenylacetylene (0.2mmol), compound 2 (82mg, 0.2mmol), NaBH 4 (3.8mg, 0.4mmol), was added to 1mL water and 0.8mL triethylamine, then added catalyst Pd(PPh 3 ) 4 (0.008mmol) and CuI (0.004mmol), under argon protection, heated and stirred at 80°C for 4h, until the TLC detection substrate disappeared, and the reaction ended; the reaction solution was distilled under reduced pressure to remove the organic solvent to obtain a viscous liquid;

[0068] (2) the viscous liquid obtained in step (1) is subjected to silica gel column chromatography (eluent is V 石油醚 :V 乙酸乙酯 =5:1) Compound 3a was obtained with a yield of 65%.

Embodiment 3

[0070] A preparation method of N-vinyl-1,2,3-triazole compounds, the reaction process is as formula (3) in Example 1; the difference is:

[0071] (1) Compound 1a, namely phenylacetylene (34uL, 0.3mmol), compound 2 (82mg, 0.2mmol), NaBH 4 (3.8mg, 0.4mmol), was added in 1mL methanol and 1mL triethylamine, then added catalyst Pd(PPh 3 ) 4 (0.004mmol) and CuCl 2 (1.4mg, 0.008mmol), protected by argon, heated and stirred at 60°C for 4h, until the substrate disappeared as detected by TLC, and the reaction was completed; the reaction solution was distilled under reduced pressure to remove the organic solvent to obtain a viscous liquid;

[0072] (2) the viscous liquid obtained in step (1) is subjected to silica gel column chromatography (eluent is V 石油醚 :V 乙酸乙酯 =5:1) to obtain compound 3a with a yield as high as 88%.

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Abstract

The invention belongs to the technical field of organic synthesis chemistry and particularly relates to a preparation method of an N-vinyl-1,2,3-triazole compound. The preparation method comprises thefollowing steps: firstly, adding a terminal alkyne compound 1, a compound 2 and a nucleophilic reagent Nu into a solvent containing triethylamine; then, adding a Pd/Cu catalyst into a reaction system, heating for reaction under the protection of argon, where the reaction ends after a substrate disappears; secondly, carrying out vacuum distillation on reaction liquid obtained in the first step, removing an organic solvent, and eluting the obtained liquid to obtain the N-vinyl-1,2,3-triazole compound. The N-vinyl-1,2,3-triazole is obtained by adopting a method for in situ generation of 2-azidopropylene and derivatives thereof. The method has the advantages of extremely-simple operation, simple and easily-obtained substrates and catalysts, excellent universality of the substrates, good tolerance of functional groups and insensitivity to the ambient atmosphere and uniform and excellent yield.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis chemistry, and in particular relates to a preparation method of N-vinyl-1,2,3-triazole compounds. Background technique [0002] 1,2,3-Triazole and its derivatives have a wide range of applications, including organic synthesis (Angew.Chem.Int.Ed,, 2014,53,3868), material science (Chem.Rev,2016,116 ,5689), biochemistry (Chem.Rev.,2016,116,3086) and drug synthesis (J.Am.Chem.Soc.,2017,139,3756). As part of them, N-vinyl-substituted 1,2,3-triazoles are important precursors for industrially functionalized polymers. Many chemists have used the easy polymerization properties of N-vinyl-1,2,3-triazole to produce electron-rich polymers on a large scale (Polym. Chem., 2012, 3, 1680). At present, there are two general methods for the preparation of N-vinyl-1,2,3-triazole. One is to post-modify NH / sulfonyl-triazole with electrophile under suitable conditions (Bioorg .Med.Chem.Lett.,2009,19,3899; ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D249/06C07D409/04C07D249/04
CPCC07D249/04C07D249/06C07D409/04
Inventor 唐波郝文静刘振华高雯
Owner SHANDONG NORMAL UNIV
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