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Preparation method of axially chiral aryl triazole compound

A kind of aryl triazole and compound technology, which is applied in the field of preparation of axial chiral aryl triazole compounds

Pending Publication Date: 2022-06-28
ZHEJIANG UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the preparation of axially chiral aryltriazoles using the stereoselective cycloaddition reaction of alkynes and azides to construct chiral axes has not been reported.

Method used

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  • Preparation method of axially chiral aryl triazole compound
  • Preparation method of axially chiral aryl triazole compound
  • Preparation method of axially chiral aryl triazole compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0063] 1-Phenylethynyl-2-naphthol (24.5 mg, 0.1 mmol), [Rh(cod)(OH)] were weighed into a reaction tube 2 (0.5 mg, 0.001 mmol), (S)-(+)-(3,5-dioxa-4-phosphocyclohepta[2,1-a;3,4-a']dinaphthalene-4- base)-5hydro-dibenzo[b,f]azepine (1.1 mg, 0.002 mmol), dichloromethane (1 mL) was added, followed by benzyl azide (16 mg, 0.12 mmol), the reaction was left open for 2 hours at room temperature, TLC detected that the reaction was completely converted, and the reaction solution was directly passed through silica gel The product was obtained by column chromatography (eluent: petroleum ether:ethyl acetate=3:1), the yield was 95%, and the ee value was 94%.

[0064] 1-Phenylethynyl-2-naphthol (24.5 mg, 0.1 mmol), [Rh(cod)(OH)] were weighed into a reaction tube 2 (0.5 mg, 0.001 mmol), (R)-(-)-(3,5-dioxa-4-phosphocyclohepta[2,1-a;3,4-a']dinaphthalene-4- base)-5hydro-dibenzo[b,f]azepine (1.1 mg, 0.002 mmol), dichloromethane (1 mL) was added, followed by benzyl azide (16 mg, 0.12 mmol), t...

Embodiment 2

[0072] 1-Phenylethynyl-2-naphthol (24.5 mg, 0.1 mmol), [Rh(cod)(OH)] were weighed into a reaction tube 2 (0.5 mg, 0.001 mmol), (S)-(+)-(3,5-dioxa-4-phosphocyclohepta[2,1-a;3,4-a']dinaphthalene-4- base)-5hydro-dibenzo[b,f]azepine (1.1 mg, 0.002 mmol), dichloromethane (1 mL) was added, followed by phenyl azide (14 mg, 0.12 mmol), the reaction was left open for 2 hours at room temperature, TLC detected that the reaction was completely converted, and the reaction solution was directly passed through silica gel The product was obtained by column chromatography (eluent: petroleum ether:ethyl acetate=3:1), the yield was 98%, and the ee value was 94%.

[0073] 1-Phenylethynyl-2-naphthol (24.5 mg, 0.1 mmol), [Rh(cod)(OH)] were weighed into a reaction tube 2(0.5 mg, 0.001 mmol), (R)-(-)-(3,5-dioxa-4-phosphocyclohepta[2,1-a;3,4-a']dinaphthalene-4- base)-5hydro-dibenzo[b,f]azepine (1.1 mg, 0.002 mmol), dichloromethane (1 mL) was added, followed by phenyl azide (14 mg, 0.12 mmol), th...

Embodiment 3

[0080] 1-Phenylethynyl-2-naphthol (24.5 mg, 0.1 mmol), [Rh(cod)(OH)] were weighed into a reaction tube 2 (0.5 mg, 0.001 mmol), (S)-(+)-(3,5-dioxa-4-phosphocyclohepta[2,1-a;3,4-a']dinaphthalene-4- base)-5hydro-dibenzo[b,f]azepine (1.1 mg, 0.002 mmol), dichloromethane (1 mL) was added, then 2-fluorophenyl azide (16.5 mg, 0.12 mmol) was added, and the reaction was left open for 4 hours at room temperature. The liquid was directly separated by silica gel column chromatography (eluent: petroleum ether:ethyl acetate=3:1) to obtain 34.7 mg of the product, the yield was 91%, and the ee value was 91%.

[0081] 1-Phenylethynyl-2-naphthol (24.5 mg, 0.1 mmol), [Rh(cod)(OH)] were weighed into a reaction tube 2 (0.5 mg, 0.001 mmol), (R)-(-)-(3,5-dioxa-4-phosphocyclohepta[2,1-a;3,4-a']dinaphthalene-4- base)-5hydro-dibenzo[b,f]azepine (1.1 mg, 0.002 mmol), dichloromethane (1 mL) was added, then 2-fluorophenyl azide (16.5 mg, 0.12 mmol) was added, and the reaction was left open for 4 hou...

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Abstract

The invention discloses a preparation method of an axially chiral aryl triazole compound. The preparation method comprises the following step: carrying out cycloaddition reaction on a 1-alkynyl-2-naphthol or o-alkynylphenol compound and an organic azide compound in a solvent under the synergistic effect of a metal catalyst and a chiral phosphoramidite ligand with a specified configuration. And after the reaction is completed, carrying out post-treatment to obtain the aryl triazole compound with the single configuration. The preparation method utilizes classical Click reaction of alkyne and azide to construct a chiral axis under mild conditions, the reaction is efficient, simple and rapid, the yield, regioselectivity and stereoselectivity are very high, and the method has very important significance in the fields of axial chiral construction and Click chemistry, and has profound application potential in organic synthesis, pharmaceutical chemistry and chemical biology.

Description

technical field [0001] The invention belongs to the field of organic synthesis, in particular to a preparation method of an axial chiral aryl triazole compound. Background technique [0002] Axial chirality widely exists in natural products, drug molecules, chiral catalysts and chiral ligands. In the past two decades, the study of axial chirality has become a hot spot in organic asymmetric synthesis. Many research groups at home and abroad have developed various Axial chiral compounds were constructed in a similar way (Chem. Rev. 2021, 121, 4805-4902; Chem. Rev. 2011, 111, 563-639; J. Am. Chem. Soc. 2021, 143, 14025-14040). However, developing precise and controllable axial chirality construction methods remains challenging. [0003] Triazole structures have very important applications in chemistry, biology, and materials science. Its most important synthetic method is the Huisgen cycloaddition reaction that relies on alkynes and organic azides, and the reaction formula is...

Claims

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Application Information

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IPC IPC(8): C07D249/06C07D401/04C07D403/04C07D405/06C07D409/06C07D405/04C07D403/06C07D409/04C07F7/08
CPCC07D249/06C07D401/04C07D403/04C07D405/06C07D409/06C07D405/04C07D403/06C07D409/04C07F7/0814C07F7/083C07B2200/07
Inventor 崔孙良曾林伟李嘉铭
Owner ZHEJIANG UNIV
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