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Preparation method and application of novel 5-thiocyanate substituted 1,4,5-trisubstituted 1,2,3-triazole

A thiocyanate, tri-substituted technology, applied in the field of preparation of 1,2,3-triazole, achieves the effects of mild reaction conditions and high reaction efficiency

Inactive Publication Date: 2019-12-20
DALIAN UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, for the cycloaddition reaction involving an azide-thiocyanate-based internal alkyne to generate a 5-thiocyanate-substituted 1,4,5-trisubstituted 1,2,3-triazole, Not yet reported in the literature
But there are no related reports
Although some azide-thio internal alkyne cycloaddition reactions have been reported to prepare 5-thio-1,4,5-trisubstituted 1,2,3-triazoles (Angew.Chem.Int .Ed.2017,56,10766 and Angew.Chem.Int.Ed.2014,53,1877), but for the preparation of 5-thio- The technology of 1,4,5-trisubstituted 1,2,3-triazole still needs to be further expanded

Method used

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  • Preparation method and application of novel 5-thiocyanate substituted 1,4,5-trisubstituted 1,2,3-triazole
  • Preparation method and application of novel 5-thiocyanate substituted 1,4,5-trisubstituted 1,2,3-triazole
  • Preparation method and application of novel 5-thiocyanate substituted 1,4,5-trisubstituted 1,2,3-triazole

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] Example 1: Preparation of 5-thiocyanate-(1-benzyl)-4-phenyl-1H-1,2,3-triazole

[0031] Under air, 1-phenylethynyl thiocyanate (0.2mmol, 32.0mg) was dissolved in tetrahydrofuran (2mL), and benzyl azide (0.3mmol, 40.2mg) and [Cp*Ru(COD) Cl] (0.005mmol, 1.9mg), the reaction mixture was stirred at room temperature, reacted for 12h, spin-dried and separated by column chromatography to obtain 48mg of white solid product with a yield of 82%.

[0032]

[0033] Mp=88-90℃.. 1 H NMR (400MHz, CDCl 3 ,TMS):δ7.98-7.95(m,2H),7.55-7.48(m,3H),7.42-7.37(m,5H),5.80(s,2H). 13 C NMR (100MHz, CDCl 3 ): δ152.0, 133.4, 129.7, 129.3, 129.1, 129.0, 128.5, 127.9, 127.7, 112.3, 106.2, 53.6. HRMS (ESI-TOF) m / z calcd for C 16 h 12 N 4 S(M+Na) + 315.0674,found 315.0679.

Embodiment 2

[0034] Example 2: Preparation of 5-thiocyanate-(1-benzyl)-4-p-methoxyphenyl-1H-1,2,3-triazole

[0035] Under air, 1-p-methoxyphenylethynyl thiocyanate (0.2mmol, 37.8mg) was dissolved in tetrahydrofuran (2mL), and benzyl azide (0.3mmol, 40.2mg) and [Cp* Ru(COD)Cl] (0.005mmol, 1.9mg), the reaction mixture was stirred at room temperature, reacted for 12h, spin-dried and separated by column chromatography to obtain 50mg of white solid product with a yield of 78%.

[0036]

[0037] Mp=132-134°C. 1 H NMR (400MHz, CDCl 3 ,TMS):δ7.93(d,J=8.0Hz,2H),7.40-7.37(m,3H),7.05(d,J=8.0Hz,2H),5.79(s,2H),3.89(s, 3H). 13 C NMR (100MHz, CDCl 3 ): δ160.8, 151.9, 133.5, 129.3, 129.1, 127.9, 121.0, 114.4, 111.3, 106.4, 55.4, 53.5. HRMS (ESI-TOF) m / z calcd for C 17 h 14 N 4 OS(M+Na)+ 345.0781,found 345.0784.

Embodiment 3

[0038] Example 3: Preparation of 5-thiocyanate-(1-benzyl)-4-p-methylphenyl-1H-1,2,3-triazole In air, 1-p-methyl Phenylethynyl thiocyanate (0.2mmol, 34.6mg) was dissolved in tetrahydrofuran (2mL), then benzyl azide (0.3mmol, 40.2mg) and [Cp*Ru(COD)Cl] (0.005mmol, 1.9 mg), the reaction mixture was stirred at room temperature, reacted for 12 h, spin-dried and separated by column chromatography to obtain 47 mg of a white solid product with a yield of 77%.

[0039]

[0040] Mp=57-59°C. 1 H NMR (400MHz, CDCl 3 ,TMS):δ7.83(d,J=8.0Hz,2H),7.40-7.32(m,5H),7.31(d,J=8.0Hz,2H),5.78(s,2H),2.41(s, 3H). 13 C NMR (100MHz, CDCl 3 ): δ154.6, 147.3, 134.2, 132.8, 130.3, 129.2, 129.1, 129.1, 128.9, 128.5, 127.9, 53.1, 21.9. HRMS (ESI-TOF) m / z calcd for C 17 h 14 N 4 S(M+Na) + 329.0831,found 329.0835.

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Abstract

The invention belongs to the technical field of organic synthesis, and provides a preparation method and application of a novel 5-thiocyanate substituted 1,4,5-trisubstituted 1,2,3-triazole. The preparation method of the 5-thiocyanate substituted 1,4,5-trisubstituted 1,2,3-triazole and a preparation method of 5-thio-1,4,5-trisubstituted 1,2,3-triazole have mild reaction conditions, and the productyields are not less than 62%. The preparation methods have the mild reaction conditions, are environmentally friendly and have high reaction efficiency, and the methods are more suitable for large-scale production requirements; and the prepared 5-thio-1,4,5-trisubstituted 1,2,3-triazole compound has potential physiological activity.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and relates to a preparation method of a novel 5-thio-1,4,5-trisubstituted 1,2,3-triazole, including 1,4 substituted by 5-thiocyanate , A method for preparing 5-trisubstituted 1,2,3-triazoles and a method for preparing 5-thio-1,4,5-trisubstituted 1,2,3-triazoles. Background technique [0002] The azide-alkyne cycloaddition reaction is one of the most important methods for the preparation of 1,2,3-triazoles. In recent years, a series of documents or patents have reported the preparation methods of 1,2,3-triazole compounds. However, for the cycloaddition reaction involving an azide-thiocyanate-based internal alkyne to generate a 5-thiocyanate-substituted 1,4,5-trisubstituted 1,2,3-triazole, Not yet reported in the literature. How to realize the cycloaddition reaction of azide-thiocyanate alkynes and improve the regioselectivity of the reaction is the focus of our attention. 5-thiocyan...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D249/06
CPCC07D249/06
Inventor 宋汪泽李明董锟郑玉斌
Owner DALIAN UNIV OF TECH
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