Novel preparation method of 5-sulfonyl-1,4,5-trisubstituted 1,2,3-triazole

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

Inactive Publication Date: 2019-01-18
DALIAN UNIV OF TECH
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Although some methods for modifying the regioselectivity of internal alkyne-azido cycloaddition reactions have been reported, for 5-sulfonyl-1,4,5-trisubstituted 1,2,3-triazole The preparation technology has not yet been publicly reported

Method used

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  • Novel preparation method of 5-sulfonyl-1,4,5-trisubstituted 1,2,3-triazole
  • Novel preparation method of 5-sulfonyl-1,4,5-trisubstituted 1,2,3-triazole
  • Novel preparation method of 5-sulfonyl-1,4,5-trisubstituted 1,2,3-triazole

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0021] Example 1: Preparation of 5-benzenesulfonyl-(1-benzyl)-4-phenyl-1H-1,2,3-triazole

[0022] Under air, 1-phenylethynylphenylsulfide (0.2mmol, 42.0mg) was dissolved in chloroform (2mL), and benzyl azide (0.3mmol, 40.2mg) and [Rh(CO) 2 Cl] 2 (0.005mmol, 1.9mg), stirred the reaction mixture at 40°C, reacted for 12h, then added m-chloroperoxybenzoic acid (0.6mmol, 103.5mg), reacted at room temperature for 3h, and separated by column chromatography after the reaction to obtain 62mg of a yellow solid product , yield 80%.

[0023]

[0024] Mp=139-141°C. 1 H NMR (400MHz, CDCl 3 , TMS): δ7.78(d, J=8.0Hz, 2H), 7.58(t, J=8.0Hz, 1H), 7.52(t, J=8.0Hz, 1H), 7.46-7.38(m, 4H) ,7.21(t,J=8.0Hz,1H),7.19-7.13(m,2H),6.84-6.79(m,4H),4.34(t,J=8.0Hz,2H),3.12(t,J=8.0 Hz,2H). 13 C NMR (100MHz, CDCl 3 ): δ145.2, 140.9, 139.6, 136.4, 133.5, 130.5, 129.8, 129.0, 128.8, 128.6, 128.6, 127.8, 127.1, 124.1, 49.9, 36.3. HRMS (ESI-TOF) m / z calcd for C 22 h 19 N 3 o 2 S(M+Na) + 412.1090,foun...

Embodiment 2

[0025] Example 2: Preparation of 5-benzenesulfonyl-(1-benzyl)-4-p-methoxyphenyl-1H-1,2,3-triazole

[0026] Under air, 1-p-methoxyphenylethynylphenylsulfide (0.2mmol, 48.0mg) was dissolved in chloroform (2mL), and then benzyl azide (0.3mmol, 40.2mg) and [Rh(CO ) 2 Cl] 2 (0.005mmol, 1.9mg), stirred the reaction mixture at 40°C, reacted for 12h, then added m-chloroperoxybenzoic acid (0.6mmol, 103.5mg), reacted at room temperature for 3h, and separated by column chromatography after the reaction to obtain a colorless liquid product 61 mg, yield 75%.

[0027]

[0028] 1 HNMR (400MHz, CDCl 3 , TMS): δ7.57(d, J=8.0Hz, 2H), 7.42(t, J=8.0Hz, 1H), 7.35-7.33(m, 5H), 7.18-7.12(m, 4H), 6.96( d, J=12.0Hz, 2H), 6.06(s, 2H), 3.88(s, 3H). 13 C NMR (100MHz, CDCl 3 ): δ160.7, 150.1, 140.0, 134.7, 133.9, 131.8, 131.5, 128.9, 128.8, 128.5, 128.1, 127.0, 121.1, 113.6, 55.3, 54.5. HRMS (ESI-TOF) m / z calcd for C 22 h 19 N 3 o 3 S(M+Na) + 428.1039, found 428.1043.

Embodiment 3

[0029] Example 3: Preparation of 5-benzenesulfonyl-(1-benzyl)-4-p-bromophenyl-1H-1,2,3-triazole

[0030] Under air, 1-p-bromophenylethynylphenylsulfide (0.2mmol, 57.6mg) was dissolved in chloroform (2mL), and benzyl azide (0.3mmol, 40.2mg) and [Rh(CO) 2 Cl] 2 (0.005mmol, 1.9mg), stirred the reaction mixture at 40°C, reacted for 12h, then added m-chloroperoxybenzoic acid (0.6mmol, 103.5mg), reacted at room temperature for 3h, and separated by column chromatography after the reaction to obtain 64mg of white solid product , yield 71%.

[0031]

[0032] Mp=141-143°C. 1 H NMR (400MHz, CDCl 3 ,TMS):δ7.57(dd,J=12.0,8.0Hz,4H),7.44(t,J=8.0Hz,1H),7.36-7.34(m,5H),7.20-7.13(m,4H), 6.06(s,2H). 13 C NMR (100MHz, CDCl 3 ): δ149.0, 139.7, 134.5, 134.2, 132.5, 131.7, 131.4, 129.0, 128.9, 128.6, 128.1, 127.8, 127.0, 124.3, 54.5. HRMS (ESI-TOF) m / z calcd for C 21 h 16 BrN 3 o 2 S(M+Na) +476.0039,found 476.0042.

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Abstract

The invention belongs to the technical field of organic synthesis and provides a novel preparation method of 5-sulfonyl-1,4,5-trisubstituted 1,2,3-triazole. The novel preparation method comprises thesteps: catalyzing a thioethyne compound to react with azide in an organic solvent under the action of a rhodium carbonyl chloride dimer catalyst; then, adding 3-chloroperoxybenzoic acid; and preparing5-sulfonyl-1,4,5-trisubstituted 1,2,3-triazole by using a 'one-pot method'. The preparation method of 5-sulfonyl-1,4,5-trisubstituted 1,2,3-triazole is mild in reaction condition and the yield of notlower than 55%. The preparation method is mild in reaction condition, green, high in reaction efficiency and more meets the requirement for large-scale production, and the prepared 5-sulfonyl-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-sulfonyl-1,4,5-trisubstituted 1,2,3-triazole. 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. [0003] Since the copper-catalyzed azide-terminal alkyne cycloaddition reaction was reported by the Medal research group and the Sharpless research group in 2001 (J.Org.Chem., 2002, 67, 3057 and Angew.Chem.Int.Ed., 2002,41,2596), this reaction has received extensive research and attention. However, for copper-catalyzed azide-sulfonyl internal alkyne cycloaddition reactions, 4-sulfonyl-1,4,5-trisubstituted 1,2,3-triazoles and 5-sulfonyl Mixtures of acyl-1,4,5-trisubstituted 1,2,3-triazoles (J.Org.Chem. 2008, 73, 8057). How to chang...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D249/06C07D249/04
CPCC07D249/04C07D249/06
Inventor 宋汪泽郑楠郑玉斌
Owner DALIAN UNIV OF TECH
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