Novel 4-allyl acetate substituted N-sulfonyl 1,2,3-triazole and preparation method thereof

A kind of technology of allyl acetate and triazole, applied in the field of organic synthesis, can solve the problems such as no public report of preparation technology, and achieve the effects of high reaction efficiency and mild reaction conditions

Inactive Publication Date: 2017-07-21
DALIAN UNIV OF TECH
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although some methods for the preparation of stable N-sulfonyl-1,2,3-triazoles have been reported, for 4-allyl acetate substituted N-sulfonyl 1,2,3 -The preparation technology of triazole has not been published yet

Method used

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  • Novel 4-allyl acetate substituted N-sulfonyl 1,2,3-triazole and preparation method thereof
  • Novel 4-allyl acetate substituted N-sulfonyl 1,2,3-triazole and preparation method thereof
  • Novel 4-allyl acetate substituted N-sulfonyl 1,2,3-triazole and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] Example 1: Preparation of (E)-1-(1-methylsulfonyl-1H-1,2,3-triazole 4-alkynyl)-3-phenylallyl acetate

[0023] Under nitrogen protection, (E)-1-phenyl-1,4-enyne-3-acetate (0.4mmol, 80mg) was dissolved in toluene (2mL), and then methanesulfonyl azide (0.4 mmol, 48.4mg) and CuTC (0.02mmol, 3.8mg), the reaction mixture was stirred at room temperature, and reacted for 16h. After the reaction, saturated NH 4 Cl solution was used to quench the reaction, then extracted with organic solvent, washed with saturated NaCl solution, dried over anhydrous sodium sulfate, the combined solution was distilled under reduced pressure, and separated by column chromatography to obtain 100 mg of yellow liquid product with a yield of 78%.

[0024] 1 H-NMR (500MHz, CDCl 3 ):δ2.16(s,3H),3.56(s,3H),6.52(dd,J=15.5,1.5Hz,1H),6.61(d,J=1.5Hz,1H),6.80(d,J= 15.5Hz,1H),7.28-7.40(m,3H),7.43-7.47(m,2H),8.17(s,1H). 13 C-NMR (100MHz, CDCl 3 ): δ21.4, 43.0, 68.6, 122.3, 124.0, 127.1, 128.8, 128.9, 135.2,...

Embodiment 2

[0025] Example 2: (E)-2-methyl-1-(1-methylsulfonyl-1H-1,2,3-triazole 4-alkynyl)-3-phenylallyl acetate preparation

[0026] Under nitrogen protection, (E)-1-phenyl 2-methyl-1,4-enyne-3-acetate (0.4mmol, 86mg) was dissolved in toluene (2mL), and methanesulfonyl Azide (0.4mmol, 48.4mg) and CuTC (0.02mmol, 3.8mg), the reaction mixture was stirred at room temperature, and reacted for 16h. 4 The reaction was quenched with Cl solution, extracted with organic solvent, washed with saturated NaCl solution, dried over anhydrous sodium sulfate, the combined solution was distilled under reduced pressure, and separated by column chromatography to obtain 96 mg of yellow liquid product with a yield of 72%.

[0027] 1 H-NMR (400MHz, CDCl 3 ):δ1.89(s,3H),2.17(s,3H),3.56(s,3H),6.55(s,1H),6.67(s,1H),7.20-7.40(m,5H),8.15( s, 1H). 13 C-NMR (100MHz, CDCl 3 ): δ14.7, 21.3, 42.9, 73.2, 122.3, 127.4, 128.5, 129.3, 129.8, 133.5, 136.6, 146.4, 169.9. HRMS (ESI) Calcd for C 15 h 18 N 3 o 4 S[M+H...

Embodiment 3

[0028] Example 3: (E)-3-(3-methoxyphenyl)-1-(1-methylsulfonyl-1H-1,2,3-triazol4-alkynyl)-3-allyl Preparation of Glycolacetate

[0029] Under nitrogen protection, dissolve (E)-1-(3-methoxyphenyl)-1,4-enyne-3-acetate (0.4mmol, 92mg) in toluene (2mL), and add Methanesulfonyl azide (0.4mmol, 48.4mg) and CuTC (0.02mmol, 3.8mg), the reaction mixture was stirred at room temperature, and reacted for 16h. 4 Cl solution was used to quench the reaction, and then extracted with organic solvent, washed with saturated NaCl solution, dried over anhydrous sodium sulfate, the combined solution was distilled under reduced pressure, and separated by column chromatography to obtain 119 mg of yellow liquid product with a yield of 85%.

[0030] 1 H-NMR (400MHz, CDCl 3 ): δ2.10(s,3H),3.53(s,3H),3.79(s,3H),6.48(dd,J=15.8,1.8Hz,1H),6.60(d,J=1.8Hz,1H) ,6.72(d,J=15.8Hz,1H),6.81-6.83(m,1H),6.89-6.91(m,1H),6.98-7.01(m,1H),7.20-7.30(m,1H),8.15 (s,1H). 13 C-NMR (100MHz, CDCl 3 ): δ21.3, 42.9, 55.5, 6...

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Abstract

The invention belongs to the technical field of organic synthesizing and provides novel 4-allyl acetate substituted N-sulfonyl 1,2,3-triazole and a preparation method thereof. The preparation method includes: in an inert solvent and under the action of a thiophene-2-copper formate catalyst, catalyzing (E)-1-aryl-1,4-eneyne-3-acetate compounds and sulfonyl azide to prepare the 4-allyl acetate substituted N-sulfonyl 1,2,3-triazole. The preparation method has the advantages that the method is mild in reaction condition, green, high in reaction efficiency and capable of satisfying large-scale production requirements, product yield is not lower than 70%, and the prepared 4-allyl acetate substituted N-sulfonyl 1,2,3-triazole has potent physiological activity.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and relates to a novel 4-allyl acetate-substituted N-sulfonyl 1,2,3-triazole and a preparation method thereof. Background technique [0002] The terminal alkyne-azido 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] In 2001, the Medal research group and the Sharpless research group respectively reported the copper-catalyzed terminal alkyne-azide cycloaddition reaction (J.Org.Chem., 2002, 67, 3057 and Angew.Chem.Int.Ed., 2002, 41, 2596). Subsequently, this reaction has been extensively studied and paid attention to. Due to its excellent performance in the fields of chemistry and biology, the concept of "click chemistry" was proposed based on this reaction. However, when sulfonyl azide is used for copper-cataly...

Claims

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Application Information

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