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The synthetic method of α-cyano quaternary carbon substituted tetrahydroisoquinoline compound

A technology of tetrahydroisoquinoline and cyanoquaternary carbon, which is applied in the synthesis of isoquinoline compounds and the synthesis field of α-cyanoquaternary carbon substituted tetrahydroisoquinoline compounds, which can solve the problem of narrow substrate application range, Harsh reaction conditions, complex reaction process and other problems, to achieve the effect of convenient and practical reaction operation, mild reaction conditions and high activity

Active Publication Date: 2022-06-21
XI'AN PETROLEUM UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] Although some research progress has been made in the synthesis of α-cyanoquaternary carbon-substituted tetrahydroisoquinolines, there are still some problems, such as harsh reaction conditions, narrow scope of substrate application, introduction and removal of protective agents. In addition to complicating the reaction process and increasing by-products, it is of great research value and practical significance to study an efficient synthetic method to synthesize α-cyanoquaternary carbon-substituted tetrahydroisoquinoline compounds.

Method used

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  • The synthetic method of α-cyano quaternary carbon substituted tetrahydroisoquinoline compound
  • The synthetic method of α-cyano quaternary carbon substituted tetrahydroisoquinoline compound
  • The synthetic method of α-cyano quaternary carbon substituted tetrahydroisoquinoline compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] Embodiment 1 A kind of synthetic method of 1-phenyl-1-cyano-2-methyl-1,2,3,4-tetrahydroisoquinoline

[0034] This embodiment provides a method for synthesizing 1-phenyl-1-cyano-2-methyl-1,2,3,4-tetrahydroisoquinoline, which is to weigh 103.7 mg of 1-phenyl- 3,4-dihydroisoquinoline and 212.9 mg of methyl iodide were added to 3 mL of 1,2-dichloroethane, dissolved with continuous stirring, heated to 40°C, maintained at 40°C for 30 minutes, kept stirring and lowered to room temperature, and then 99.2 mg of trimethylsilane cyanide, 58.1 mg of potassium fluoride and 26.5 mg of sodium carbonate were added, and the addition reaction was carried out with continuous stirring at room temperature for 24 hours. After the completion of the reaction was detected by TLC, the reaction solution was extracted with dichloromethane and purified by column chromatography. , that is, 113.7 mg of 1-phenyl-1-cyano-2-methyl-1,2,3,4-tetrahydroisoquinoline was obtained, and its NMR chart is shown i...

Embodiment 2～11

[0037] Examples 2-11 Synthetic method of 1-phenyl-1-cyano-2-methyl-1,2,3,4-tetrahydroisoquinoline

[0038] Examples 2 to 11 respectively provide a method for synthesizing 1-phenyl-1-cyano-2-methyl-1,2,3,4-tetrahydroisoquinoline, and the synthesis methods are the same as those in the examples 1 is basically the same, the only difference is that the raw materials and some process parameters are different. The specific data are shown in Table 1.

[0039] Table 1: Synthesis method process parameter table of 1-phenyl-1-cyano-2-methyl-1,2,3,4-tetrahydroisoquinoline provided by Examples 2-11

[0040]

[0041] Other steps are the same as in Example 1, and the obtained products are all 1-phenyl-1-cyano-2-methyl-1,2,3,4-tetrahydroisoquinoline, and the structural formula is

Embodiment 12

[0042] Example 12 A synthetic method of 1-cyano-2-methyl-1-(3-tolyl)-1,2,3,4-tetrahydroisoquinoline

[0043] This embodiment provides a method for synthesizing 1-cyano-2-methyl-1-(3-tolyl)-1,2,3,4-tetrahydroisoquinoline, which is to weigh 110.6 mg of 1 -(3-Tolyl)-3,4-dihydroisoquinoline, 212.9 mg of methyl iodide, were added to 3 mL of 1,2-dichloroethane, stirred continuously to dissolve, heated to 40 °C, maintained at 40 °C for 30 min , continue to stir and cool to room temperature, then add 99.2 mg of trimethyl cyanosilane, 58.1 mg of potassium fluoride and 26.5 mg of sodium carbonate, and continue to stir at room temperature to carry out the addition reaction for 48 h. After the reaction is detected by TLC, dichloromethane is used. The reaction solution was extracted and purified by column chromatography to obtain 130.3 mg of 1-cyano-2-methyl-1-(3-tolyl)-1,2,3,4-tetrahydroisoquinoline, yield 99%, the chemical reaction formula is

[0044]

[0045] 2-Methyl-1-(m-tolyl)-1...

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Abstract

The invention belongs to the field of organic synthesis, and discloses a synthesis method of α-cyano quaternary carbon-substituted tetrahydroisoquinoline compounds. Addition reaction occurs to obtain α-cyanoquaternary carbon-substituted tetrahydroisoquinoline compound. The operation of the invention is simple and practical, the reaction conditions are mild, and the yield and purity of the obtained product are high. The invention is suitable for the synthesis of isoquinoline compounds, especially for the synthesis of α-cyano quaternary carbon-substituted tetrahydroisoquinoline compounds.

Description

technical field [0001] The invention belongs to the field of organic synthesis and relates to a method for synthesizing isoquinoline compounds, in particular to a method for synthesizing α-cyano quaternary carbon substituted tetrahydroisoquinoline compounds. Background technique [0002] In the prior art, tetrahydroisoquinoline compounds, as a class of important organic amine compounds, widely exist in natural products and biologically active molecules. Chiral tetrahydroisoquinoline alkaloids usually have very good biological activities, and are also an important class of pharmaceutical intermediates, which are closely related to the life activities of the human body. Among them, the C-1 quaternary carbon substituted tetrahydroisoquinoline compounds have rich biological activities. For example, the C-1 quaternary carbon substituted tetrahydroisoquinoline compound MK-801, also known as dizocilpine / dizocilpine, belongs to an effective and highly selective NMDA (N-methyl-D- A...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D217/26
CPCC07D217/26
Inventor 姬悦张学韩薇薇王嗣昌吴亚刘雪梅
Owner XI'AN PETROLEUM UNIVERSITY
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