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Method for preparing triazol isoquinoline derivatives

A technology of triazole derivatives and derivatives, applied in the direction of organic chemistry, etc., to achieve the effect of simple preparation method and cost reduction

Inactive Publication Date: 2015-06-24
ZHEJIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] Many chemical methods for synthesizing isoquinoline derivatives have been reported, but the isoquinoline derivatives with new structures still need to be studied further. Triazoloisoquinoline derivatives are synthesized from 1,2,3-triazole compounds catalyzed by rhodium No report

Method used

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  • Method for preparing triazol isoquinoline derivatives
  • Method for preparing triazol isoquinoline derivatives
  • Method for preparing triazol isoquinoline derivatives

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] In a dry 25mL pressure-resistant reaction tube, add 51mg of 1-octyl-4-phenyl-1,2,3-triazole, 20mg of 3-hexyne, 6mg of dichloro(pentamethylcyclopentadiene alkenyl) rhodium dimer, 80 mg of copper acetate monohydrate, 32 mg of sodium peroxide, and 1.5 mL of 1,2-dichloroethane. Stir at 100°C for 24 hours. After the reaction was finished, it was cooled to room temperature and directly passed through a silica gel column (the volume ratio of ethyl acetate to petroleum ether was 1:3) to obtain 45 mg of the product with a yield of 64%. The reaction process is shown in the following formula:

[0031]

[0032] Carry out nuclear magnetic resonance analysis to the product that present embodiment prepares:

[0033] 1 H NMR (400MHz, CDCl 3): δ8.86(d, J=8Hz, 1H), 7.81(d, J=8Hz, 1H), 7.61(dd, J=7.2, 1.6Hz, 1H), 7.49(dd, J=7.2, 1.6Hz ,1H),4.28(t,J=7.2Hz,2H),3.17(q,J=7.0Hz,2H),3.03(q,J=7.0Hz,2H),1.93(t,J=6.8Hz,2H ),1.36-1.26(m,16H),0.86(t,J=6.8Hz,3H); 13 C NMR (100MHz, CDCl 3 ):...

Embodiment 2

[0035] In a dry 25mL pressure-resistant reaction tube, add 58mg of 1-octyl-4-(p-chlorophenyl)-1,2,3-triazole, 20mg of 3-hexyne, 6mg of dichloro(pentamethyl (cyclopentadienyl) rhodium dimer, 80 mg of copper acetate monohydrate, 32 mg of sodium peroxide, and 1.5 mL of 1,2-dichloroethane. Stir at 100°C for 24 hours. After the reaction was finished, it was cooled to room temperature and directly passed through a silica gel column (the volume ratio of ethyl acetate to petroleum ether was 1:3) to obtain 56 mg of product with a yield of 73%. The reaction process is shown in the following formula:

[0036]

[0037] Carry out nuclear magnetic resonance analysis to the product that present embodiment prepares:

[0038] 1 H NMR (400MHz, CDCl 3 ): δ8.79(d, J=8.8Hz, 1H), 7.77(s, 1H), 7.56(d, J=8.8Hz, 1H), 4.28(t, J=7.2Hz, 2H), 3.16(q ,J=7.2Hz,2H),2.97(q,J=7.2Hz,2H),1.93(t,J=6.8Hz,2H),1.35-1.26(m,16H),0.86(t,J=6.8Hz ,3H); 13 C NMR (100MHz, CDCl 3 ): δ153.6, 134.5, 132.3, 128.8, 12...

Embodiment 3

[0040] In a dry 25mL pressure-resistant reaction tube, add 54mg of 1-octyl-4-(p-methylphenyl)-1,2,3-triazole, 20mg of 3-hexyne, 6mg of dichloro(penta methylcyclopentadienyl) rhodium dimer, 80 mg of copper acetate monohydrate, 32 mg of sodium peroxide, and 1.5 mL of 1,2-dichloroethane. Stir at 100°C for 24 hours. After the reaction was finished, it was cooled to room temperature and directly passed through a silica gel column (the volume ratio of ethyl acetate and petroleum ether was 1:3) to obtain 45 mg of product with a yield of 62%. The reaction process is shown in the following formula:

[0041]

[0042] Carry out nuclear magnetic resonance analysis to the product that present embodiment prepares:

[0043] 1 H NMR (400MHz, CDCl 3 ): δ8.69(d, J=8.4Hz, 1H), 7.53(s, 1H), 7.37(d, J=8.0Hz, 1H), 4.21(t, J=7.2Hz, 2H), 3.09(q ,J=7.2Hz,2H),2.94(q,J=7.2Hz,2H),2.46(s,3H),1.86(t,J=7.2Hz,2H),1.28-1.19(m,16H),0.86 (t,J=6.8Hz,3H). 13 C NMR (100MHz, CDCl 3 ): δ153.5, 136.4, 133.3...

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Abstract

The invention discloses a method for preparing triazol isoquinoline derivatives. The method for preparing the triazol isoquinoline derivatives comprises the following steps: in an organic solvent environment, carrying out cyclization oxidation reaction on 1,2,3-triazol derivatives and internal alkyne in presence of a rhodium catalyst, a copper salt catalyst and an oxidizing agent, so that the triazol isoquinoline derivatives are obtained by one-pot reaction. The method for preparing the triazol isoquinoline derivatives has the advantages that 1,2,3-triazol derivatives and internal alkylne are taken as raw materials, reaction materials are cheap and available, the preparation method is simple, a small amount of the rhodium catalyst and the copper salt catalyst are taken as the catalysts, and cost can be greatly reduced. The method for preparing the triazol isoquinoline derivatives is used for synthesizing a series of triazol isoquinoline derivatives, and the obtained triazol isoquinoline derivative products have anti-tumour biological activity, anti-inflammatory biological activity and anti-bacterial biological activity and can be taken as important intermediates during complete synthesis of alkaloids.

Description

technical field [0001] The invention relates to the field of organic synthesis, in particular to a method for synthesizing triazoloisoquinoline derivatives by reacting 1,2,3-triazole derivatives with internal alkynes catalyzed by rhodium catalysts and copper salts. Background technique [0002] Isoquinoline is an important part of alkaloids and drugs, and is the core structural unit of many natural products. It has a wide range of biological activities, including antibacterial, antitumor, analgesic, antiarrhythmic, antihypertensive, immune regulation and other functions. Because isoquinoline and its derivatives are not only substructural units of many natural and synthetic compounds, but also important intermediates in the total synthesis of alkaloids, chemists are constantly striving to develop new structures based on the isoquinoline skeleton and their new synthesis method. [0003] The traditional method of synthesizing isoquinoline derivatives comprises the cyclization ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D471/04
CPCC07D471/04
Inventor 陈万芝
Owner ZHEJIANG UNIV