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Synthesis method for substituted triazole compound

A compound and catalyst technology, applied in the field of synthesis of triazole compounds, can solve the problems of limited application of catalysts, slow cycloaddition reaction, etc., and achieve the effects of simple operation and easy availability of raw materials

Inactive Publication Date: 2014-03-05
GUANGXI NORMAL UNIV
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AI Technical Summary

Problems solved by technology

[0003] The traditional synthesis method of 1,2,3-triazole compounds is through dipolar cycloaddition reaction of alkyne and organic azide, namely Huisgen condensation, however, due to high activation energy (ca.24-26kcal / mol), this kind of Cycloaddition reactions are usually slow and often give mixtures of isomers
Only 1,4-disubstituted-1,2,3-triazoles can be obtained by Cu(I)-catalyzed cycloaddition of alkynes and organic azides (CuAAC); although [Cp*Ru(II)] Catalyzed cycloaddition reaction (RuAAC) can easily and efficiently synthesize 1,5-disubstituted-1,2,3-triazoles, but expensive catalysts limit its application
Therefore, there is currently no satisfactory catalytic system for the selective synthesis of 1,5-disubstituted-1,2,3-triazole compounds

Method used

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  • Synthesis method for substituted triazole compound
  • Synthesis method for substituted triazole compound
  • Synthesis method for substituted triazole compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] Example 1: Synthesis of 1-benzyl-5-phenyl-1H-1,2,3-triazole

[0021] Add 1 mmol of β-nitrostyrene, 1 mmol of benzyl azide, 0.05 mmol of cerium trifluoromethanesulfonate and 2 mL of toluene into a 25 mL round bottom flask, and reflux the reaction at 110 ° C until complete (TLC tracking detection, about 10 h ), stop the reaction, wait for the reaction solution to be cooled to room temperature, filter, remove the solvent under reduced pressure, and purify the residue by fast silica gel column chromatography (eluent is ethyl acetate / petroleum ether=1:20, volume ratio), to obtain light Yellow oily liquid 1a, yield 85%.

[0022] Gained pale yellow oily liquid 1a is analyzed, and its spectral characteristics are as follows:

[0023] 1 H NMR (400MHz, CDCl 3 ): δ7.74(s,1H),7.47-7.34(m,3H),7.27(m,5H),7.11-7.03(m,2H),5.55(s,2H)ppm;

[0024] 13 C NMR (100MHz, CDCl 3 )δ138.15, 135.49, 133.27, 129.50, 128.94, 128.88, 128.81, 128.14, 127.14, 126.89, 51.80ppm;

[0025] HRMS(m / z)...

Embodiment 2

[0028] Example 2: Synthesis of 1-benzyl-5-(4-methylphenyl)-1H-1,2,3-triazole

[0029] Add 1mmol of 4-methyl-β-nitrostyrene, 1mmol of benzyl azide, 0.08mmol of samarium trifluoromethanesulfonate and 5mL of toluene into a 25mL round bottom flask, and reflux the reaction at 100°C until complete (TLC tracking detection , about 12h), stop the reaction, wait for the reaction solution to cool to room temperature, filter, remove the solvent under reduced pressure, and purify the residue by flash silica gel column chromatography (eluent is ethyl acetate / petroleum ether=1:10, volume ratio) , a yellow oily liquid 1b was obtained with a yield of 80%.

[0030] Gained yellow oily liquid 1b is analyzed, and its spectral characteristics are as follows:

[0031] 1 H NMR (400MHz, CDCl 3 ):δ7.71(s,1H),7.29(m,3H),7.22(d,J=8.0Hz,2H),7.14(d,J=8.1Hz,2H),7.12-7.02(m,2H) ,5.53(s,2H),2.39(s,3H)ppm;

[0032] 13 C NMR (100MHz, CDCl 3 ): δ139.62, 138.22, 135.65, 133.11, 129.63, 128.79, 128.75, 128....

Embodiment 3

[0036] Example 3: Synthesis of 1-benzyl-5-[4-(benzyloxy)-3-methoxyphenyl]-1H-1,2,3-triazole

[0037] Add 1 mmol of trans-3-benzyloxy-4-methoxy-β-nitrostyrene, 1 mmol of benzyl azide, 0.01 mmol of europium trifluoromethanesulfonate, and 2 mL of toluene into a 25 mL round-bottomed flask at 80 °C Under the conditions, the reaction was refluxed until complete (TLC tracking detection, about 48h), the reaction was stopped, and the reaction solution was cooled to room temperature, filtered, and the solvent was removed under reduced pressure, and the residue was purified by fast silica gel column chromatography (eluent was ethyl acetate / Petroleum ether=1:25, volume ratio), to obtain yellow oily liquid 1c, yield 71%.

[0038] Gained yellow oily liquid 1c is analyzed, and its spectral characteristics are as follows:

[0039] yellow oil; 1 H NMR (400MHz, CDCl 3 ):δ7.69(s,1H),7.53-7.18(m,8H),7.16-7.01(m,2H),6.90(d,J=8.3Hz,1H),6.76(dd,J=8.2,2.0 Hz,1H),6.62(d,J=1.9Hz,1H),5.52(s,2H),5.18(...

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Abstract

The invention discloses a synthesis method for a substituted triazole compound. The method mainly comprises the following steps: under the existence of a rare earth metal catalyst, performing backflow reaction to nitroolefin and organic azido in an organic solvent at 80-110DEG C, to obtain a target crude product, wherein the rare earth metal catalyst is cerium trifluoromethanesulfonate, samarium trifluoromethanesulfonate, europium trifluoromethanesulfonate, ytterbium trifluoromethanesulfonate, praseodymium trifluoromethanesulfonate, lanthanum trifluoromethanesulfonate, neodymium trifluoromethanesulfonate, erbium trifluoromethanesulfonate or dysprosium trifluoromethanesulfonate. According to the synthesis method, 1,5-disubstituted-1,2,3-triazole compound can be efficiently selectively synthesized by taking nitroolefin and organic azido as active ingredients under the action of a rare earth metal catalyst. The method is easily available for active ingredients, and simple to operate, and the productivity can achieve more than 70%.

Description

technical field [0001] The invention relates to a synthesis method of a triazole compound, in particular to a synthesis method of 1,5-disubstituted-1,2,3-triazole. Background technique [0002] 1,2,3-Triazole is an important class of nitrogen-containing heterocyclic compounds. Its azole ring is aromatic and rich in electrons. It can form hydrogen bonds, coordinate with metal ions and undergo hydrophobic interactions, and π-π stacking And electrostatic interaction and other non-covalent bond forces interact with enzymes and receptors in organisms, making triazole compounds exhibit anti-fungal, anti-bacterial, anti-tuberculosis, anti-cancer, anti-virus, anti-inflammatory analgesic and anti-convulsant and other biological activities. Triazole compounds are widely used in clinic as drugs, and triazole compounds also have a wide range of potential applications in pesticides, materials, artificial receptors, supramolecular recognition and biomimetic simulation. Sangshetti et al....

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D249/06C07D405/04C07D409/04
CPCC07D249/06C07D405/04C07D409/04
Inventor 王恒山
Owner GUANGXI NORMAL UNIV
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