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Novel method for preparing 4-sulfonyl-1,4,5-tri-substituted 1,2,3-triazole

A sulfonyl, tri-substituted technology, applied in the field of organic synthesis, can solve problems such as no public reports, and achieve the effects of high reaction efficiency and mild reaction conditions

Inactive Publication Date: 2018-12-28
DALIAN UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Although other research groups have also developed some methods to modify the regioselectivity of the internal alkyne-azido cycloaddition reaction, the preparation of 4-sulfonyl-1,4,5 by azide-internal alkyne cycloaddition reaction -The technical method of trisubstituted 1,2,3-triazole has not yet been publicly reported

Method used

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  • Novel method for preparing 4-sulfonyl-1,4,5-tri-substituted 1,2,3-triazole
  • Novel method for preparing 4-sulfonyl-1,4,5-tri-substituted 1,2,3-triazole
  • Novel method for preparing 4-sulfonyl-1,4,5-tri-substituted 1,2,3-triazole

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] Example 1: Preparation of 4-benzenesulfonyl-(1-benzyl)-5-phenyl-1H-1,2,3-triazole

[0021] Under air, 1-benzenesulfonylphenylacetylene (0.2mmol, 48.4mg) was dissolved in 1,2-dichloroethane (2mL), then benzyl azide (0.3mmol, 40.2mg) and [Rh (CO) 2 Cl] 2 (0.005mmol, 1.9mg), the reaction mixture was stirred at 40°C, and reacted for 12h. After the reaction, 61mg of a colorless oily product was obtained by column chromatography, with a yield of 81%.

[0022]

[0023] 1 H NMR (400MHz, CDCl 3 ,TMS):δ7.79(d,J=8.0Hz,2H),7.55-7.50(m,2H),7.44-7.39(dd,J=12.0,8.0Hz,4H),7.24-7.19(m,3H ), 7.11(d, J=8.0Hz, 2H), 6.93(d, J=8.0Hz, 2H), 5.32(s, 2H). 13 C NMR (100MHz, CDCl 3 ): δ145.9, 140.8, 139.3, 134.0, 133.8, 130.9, 130.2, 129.2, 129.0, 128.9, 128.8, 128.1, 128.0, 124.4, 52.8.

Embodiment 2

[0024] Example 2: Preparation of 4-benzenesulfonyl-(1-p-methylbenzyl)-5-phenyl-1H-1,2,3-triazole

[0025] Under air, 1-benzenesulfonylphenylacetylene (0.2mmol, 48.4mg) was dissolved in 1,2-dichloroethane (2mL), then p-methylbenzyl azide (0.3mmol, 44.1mg) was added and [Rh(CO) 2 Cl] 2 (0.005mmol, 1.9mg), the reaction mixture was stirred at 40°C, and reacted for 12h. After the reaction, 59mg of white solid product was obtained by column chromatography, with a yield of 76%.

[0026]

[0027] Mp=147-149°C. 1 H NMR (400MHz, CDCl 3 , TMS): δ7.83(d, J=8.0Hz, 2H), 7.57(t, J=8.0Hz, 2H), 7.50-7.43(m, 4H), 7.17(d, J=8.0Hz, 2H) ,7.05(d,J=8.0Hz,2H),6.87(d,J=8.0Hz,2H),5.31(s,2H),2.31(s,3H). 13 C NMR (100MHz, CDCl 3 ): δ145.7, 140.7, 139.1, 138.6, 133.6, 130.8, 130.7, 130.1, 129.5, 129.0, 128.7, 128.0, 127.8, 124.3, 52.4, 21.1. HRMS (ESI-TOF) m / z calcd for C 22 h 19 N 3 o 2 S(M+Na) + 412.1090,found 412.1094.

Embodiment 3

[0028] Example 3: Preparation of 4-benzenesulfonyl-(1-p-chlorobenzyl)-5-phenyl-1H-1,2,3-triazole

[0029] Under air, dissolve 1-benzenesulfonylphenylacetylene (0.2mmol, 48.4mg) in 1,2-dichloroethane (2mL), then add p-chlorobenzyl azide (0.3mmol, 50.1mg) and [Rh(CO) 2 Cl] 2 (0.005mmol, 1.9mg), the reaction mixture was stirred at 40°C, and reacted for 12h. After the reaction, 57mg of a yellow solid product was obtained by column chromatography, with a yield of 70%.

[0030]

[0031] Mp=132-134°C. 1 H NMR (400MHz, CDCl 3 , TMS): δ7.83(d, J=8.0Hz, 2H), 7.58(t, J=8.0Hz, 2H), 7.50-7.45(m, 4H), 7.22(d, J=8.0Hz, 2H) ,7.15(d,J=8.0Hz,2H),6.91(d,J=8.0Hz,2H),5.32(s,2H). 13 C NMR (100MHz, CDCl 3 ): δ145.9, 140.6, 139.1, 134.8, 133.7, 132.2, 130.9, 130.0, 129.3, 129.1, 128.8, 128.0, 124.1, 51.9. HRMS (ESI-TOF) m / z calcdfor C 21 h 16 ClN 3 o 2 S(M+Na) + 432.0544,found 432.0546.

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Abstract

The invention belongs to the technical field of organic synthesis and provides a novel method for preparing 4-sulfonyl-1,4,5-tri-substituted 1,2,3-triazole. The novel method comprises the following step: in an organic solvent, under the action of a tetracarbonyl rhodium chloride dimer catalyst, catalyzing a hydrocarbon compound in sulfonyl and nitrine, thereby obtaining the 4-sulfonyl-1,4,5-tri-substituted 1,2,3-triazole. The method for preparing the 4-sulfonyl-1,4,5-tri-substituted 1,2,3-triazole, which is provided by the invention, is gentle in reaction condition and has a product yield which is not less than 70%. The method is gentle and green in reaction condition, high in reaction efficiency and applicable to on-scale production requirements, and the prepared 4-sulfonyl-1,4,5-tri-substituted 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 4-sulfonyl-1,4,5-trisubstituted 1,2,3-triazole. Background technique [0002] According to literature reports, 4-sulfonyl-1,4,5-trisubstituted 1,2,3-triazole compounds have excellent biological activities such as antibacterial, anti-infection and anti-oxidation, and are an important class of drug parent Nuclear structure (Med.Chem.Commun.2017,8,2258 and Eur.J.Med.Chem.2016,112,60). However, how to efficiently synthesize 4-sulfonyl-1,4,5-trisubstituted 1,2,3-triazole compounds is still a problem to be solved. [0003] Methods such as organic catalysis and multi-component reaction have been used for 4-sulfonyl-1,4,5-trisubstituted 1,2,3-triazole compounds, but there are long reaction time, cumbersome reaction process, and reaction Harsh conditions and many other shortcomings (Org.Lett.2015, 17, 6206 and Angew.Chem.Int.Ed.2014, 53, 10155). T...

Claims

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Application Information

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