Preparation method of 1,4-diallyl isoquinoline

A technology of diallylisoquinoline and cyclohexenyl, which is applied in the field of 1, can solve the problems of single starting material and application limitation, and achieve the effects of short reaction time, wide range and high yield

Active Publication Date: 2015-04-01
SHANGHAI JIAO TONG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The above-mentioned existing methods all synthesize monoallyl substituted isoquinoline, and all use the substituent isoquinoline as the starting reactant, and the starting material is relatively single, so the application is limited

Method used

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  • Preparation method of 1,4-diallyl isoquinoline
  • Preparation method of 1,4-diallyl isoquinoline
  • Preparation method of 1,4-diallyl isoquinoline

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0018] Embodiment 1 1, the synthesis of 4-diallyl-3-phenylisoquinoline

[0019] The synthetic route of 1,4-diallyl-3-phenylisoquinoline is shown in the following formula:

[0020]

[0021] At room temperature, 1-(azidomethyl)-2-(phenylethynyl)benzene (11.7mg, 0.05mmol), potassium phosphate (53.1mg, 0.25mmol), Pd(PPh 3 ) 4 (2.9mg, 0.0025mmol) was put into a 5ml reaction kettle with magnetic stirring function. After completion, fill the reactor with argon and cover it with a lid. DMF (1 ml) and allyl methcarbonate (28.4 μL, 0.25 mmol) were sequentially injected into the autoclave using a syringe. The reaction kettle was stirred at room temperature for ten minutes, then heated to 100°C and continued to stir, and was taken out after 4 hours. After-treatment of the reactant, first pass the solid-liquid mixture through the column to obtain the liquid, then use water and ethyl acetate to extract the obtained liquid, combine the organic layers, dry and spin dry, and the residu...

Embodiment 2

[0023] Example 2 Synthesis of 1,4-diallyl-3-p-methoxyphenylisoquinoline

[0024] The synthetic route of 1,4-diallyl-3-p-methoxyphenylisoquinoline is shown in the following formula:

[0025]

[0026] At room temperature, 1-(azidomethyl)-2-((4-methoxyphenyl)ethynyl)benzene (13.2mg, 0.05mmol), potassium phosphate (53.1mg, 0.25mmol), Pd(PPh 3 ) 4 (3.8mg, 0.0033mmol) was put into a 5ml reaction kettle with magnetic stirring function. After completion, fill the reactor with argon and cover it with a lid. DMF (1 ml) and allyl methcarbonate (28.4 μL, 0.25 mmol) were sequentially injected into the autoclave using a syringe. The reaction kettle was stirred at room temperature for ten minutes, then heated to 100°C and continued to stir, and was taken out after 4 hours. After-treatment of the reactant, first pass the solid-liquid mixture through the column to obtain the liquid, then use water and ethyl acetate to extract the obtained liquid, combine the organic layers, dry and sp...

Embodiment 3

[0028] Example 3 Synthesis of 1,4-diallyl-7-chloro-3-phenylisoquinoline

[0029] The synthetic route of 1,4-diallyl-7-chloro-3-phenylisoquinoline is shown in the following formula:

[0030]

[0031] At room temperature, 2-(azidomethyl)-4-chloro-1-(phenylethynyl)benzene (12.4mg, 0.05mmol), potassium phosphate (53.1mg, 0.25mmol), Pd(PPh 3 ) 4 (2.9mg, 0.0025mmol) was put into a 5ml reaction kettle with magnetic stirring function. After completion, fill the reactor with argon and cover it with a lid. DMF (1 ml) and allyl methcarbonate (28.4 μL, 0.25 mmol) were sequentially injected into the autoclave using a syringe. The reaction kettle was stirred at room temperature for ten minutes, then heated to 100°C and continued to stir, and was taken out after 4 hours. After-treatment of the reactant, first pass the solid-liquid mixture through the column to obtain the liquid, then use water and ethyl acetate to extract the obtained liquid, combine the organic layers, dry and spin d...

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Abstract

The invention discloses a preparation method of 1,4-diallyl isoquinoline synthesized by using a palladium catalyst. The structural formula of 1,4-diallyl isoquinoline is shown in the specification, wherein R1 refers to one or more substituents connected to a benzene ring, and is selected from one of H, chlorine and -O-CH2-O-, and R2 is one of phenyl, p-methoxyphenyl, and 1-cyclohexenyl. In the process of preparing, 1-methyl azide-2-ethinyl-benzene shown in the specification is taken as a raw material, and reacted with allyl methyl carbonate in the presence of a Pd(PPh3)4 catalyst, an alkaline cocatalyst and an organic solvent, so that 1,4-diallyl isoquinoline is obtained. According to the invention, a 1,4-diallyl isoquinoline compound can be efficiently synthesized by using a one-pot method; the preparation method is high in conversion efficiency, short in reaction time and neutral in reaction conditions, and has no generated by-product; the method is low in raw material cost, simple in operation, low in pollution to the environment, and beneficial to industrialized production; and products are widely used, and can be used as intermediates for further synthesizing more complex compounds.

Description

technical field [0001] The invention belongs to the technical field of chemical synthesis, and in particular relates to a preparation method of 1,4-diallylisoquinoline. Background technique [0002] The isoquinoline skeleton is a common compound, which usually exists in many plants and medicines. The isoquinoline containing substituents has a wide range of applications in medicinal chemistry and organic synthesis, while the isoquinoline containing allyl substituents is one of the more important ones. It has been reported that quinoline or isoquinoline containing allyl group has special anti-leishmania drug effect , 2005, 49, 1076-1080], at the same time, allyl isoquinoline can also be used as an intermediate to synthesize other compounds, so it has received more and more attention. At present the main method of synthesizing isoquinoline with allyl is to obtain allyl isoquinoline [(a) F.Berthiol, H.Doucet, M.Santelli by monosubstituted isoquinoline and allyl ester reaction ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D217/02C07D217/16C07D491/056
CPCC07D217/02C07D217/20C07D491/056
Inventor 霍志保罗将任德章宋志远傅骏金放鸣
Owner SHANGHAI JIAO TONG UNIV
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