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Novel polysubstitution isoquinoline derivative and synthesis method thereof

A synthetic method and isoquinoline technology, applied in the direction of drug combination, antipyretics, antineoplastic drugs, etc., can solve the problems of harsh reaction conditions, large amount of catalysts, expensive raw materials, etc., and achieve less side reactions and high reactivity , The effect of easy access to raw materials

Active Publication Date: 2017-11-24
JIANGSU UNIV OF TECH
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Problems solved by technology

[0004] In order to solve the shortcomings of the prior art, such as expensive raw materials, high catalyst consumption, harsh reaction conditions, many reaction steps, and long reaction time, the present invention provides a new isoquinoline derivative and a preparation method thereof. Easy to obtain and mild reaction conditions, the isoquinoline derivatives synthesized by the present invention can be applied to the fields of medicine and agriculture

Method used

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  • Novel polysubstitution isoquinoline derivative and synthesis method thereof
  • Novel polysubstitution isoquinoline derivative and synthesis method thereof
  • Novel polysubstitution isoquinoline derivative and synthesis method thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0021] Add acetophenone oxime (0.1mmol), tolan (0.12mmol) in the reaction tube, then add pivalic acid (0.3 equivalents) and pentamethylcyclopentadiene iridium dichloride catalyst (0.025 equivalents), and then Add 1 mL of methanol, and stir the mixture at 60°C for 24 hours. After the reaction, cool the reaction system to room temperature. Suction filtration is performed after the solid precipitates, and the filtrate is rotary evaporated and dried to obtain a crude product. The crude product is separated and purified by column chromatography to obtain the target product Product 1-methyl-3,4-diphenylisoquinoline (Ia): The yield is 88%.

[0022] 1 H NMR (400MHz, CDCl 3 )δ(ppm):8.28-8.25(m,1H,ArH),7.74-7.72(m,1H,ArH),7.66-7.64(m,2H,ArH),7.45-7.39(m,5H,ArH), 7.31-7.24(m,5H,ArH),3.14(s,3H,CH 3 );

[0023] 13 C NMR (100MHz, CDCl 3 )δ (ppm): 157.9, 149.6, 147.6, 141.1, 137.7, 136.1, 131.5, 130.4, 130.0, 129.3, 128.3, 127.7, 127.2, 127.1, 126.7, 126.3, 125.7, 122.9;

[0024] HRMS...

Embodiment 2

[0026] According to the method of Example 1, 4-iodo-acetophenone oxime, with pivalic acid (0.3 equivalents) and pentamethylcyclopentadiene iridium dichloride (0.025 equivalents) as catalyst, add methanol 1mL, at 60 ℃ and stirred for 24 hours. After the reaction, the reaction system was cooled to room temperature. Suction filtration was performed after the solid was precipitated. The filtrate was rotary evaporated and dried to obtain a crude product. The crude product was separated and purified by column chromatography to obtain the target product 6-iodo-1- Methyl-3,4-diphenylisoquinoline (Ib): Yield 78%.

[0027]1 H NMR (400MHz, CDCl 3 )δ(ppm):8.04-8.03(m,1H,ArH),7.92-7.84(m,2H,ArH),7.40-7.32(m,5H,ArH),7.21-7.18(m,5H,ArH), 3.04(s,1H,CH 3 );

[0028] 13 C NMR (100MHz, CDCl 3 )δ (ppm): 158.0, 150.6, 140.8, 137.7, 136.9, 135.5, 135.2, 131.5, 130.3, 128.6, 128.1, 127.8, 127.6, 127.3, 127.1, 125.0, 197.8, 122.8;

[0029] HRMS: m / z, [M+H] + :422.04.

Embodiment 3

[0031] According to the method of Example 1, 4-nitroso-acetophenone oxime, with pivalic acid (0.3 equivalents) and pentamethylcyclopentadiene iridium dichloride (0.025 equivalents) as a catalyst, was added methanol 1mL, Stir the reaction at 60°C for 24 hours. After the reaction, cool the reaction system to room temperature. After the solid precipitates, perform suction filtration. The filtrate is rotary evaporated and dried to obtain a crude product. The crude product is separated and purified by column chromatography to obtain the target product 1-methyl -6-nitro-3,4-diphenylisoquinoline (Ic): Yield 92%.

[0032] 1 H NMR (400MHz, CDCl 3 )δ(ppm):8.60-8.59(m,1H,ArH),8.37-8.33(m,2H,ArH),7.42-7.37(m,5H,ArH),7.24-7.21(m,5H,ArH), 3.14(s,3H,CH 3 );

[0033] 13 C NMR (100MHz, CDCl 3 )δ (ppm): 158.2, 152.1, 151.8, 148.4, 140.1, 136.1, 136.0, 131.3, 130.6, 130.3, 128.9, 128.2, 128.0, 127.9, 127.7, 122.9, 120.0, 123.1;

[0034] HRMS: m / z, [M+H] + :341.13.

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Abstract

The invention provides a novel polysubstitution isoquinoline derivative shown as a formula (I) and a synthesis method thereof. The formula I is shown in the specification. A C-H activation / cyclization method is used; ketoxime and diphenylacetypene are used as raw material; pentamethyl cyclopentadiene iridochloride is used as a catalyst for synthesizing the isoquinoline derivative. The preparation method is simple; the catalyst consumption is low; the reaction conditions are mild; the reaction steps are few; the reaction time is short; the yield is high. The isoquinoline derivative provided by the invention belongs to a kind of alkaloid compounds with important medicine activity, and can be widely applied to the study in aspects of fields of medicine and agriculture.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, in particular to a novel multi-substituted isoquinoline derivative and a synthesis method thereof. Background technique [0002] Isoquinoline derivatives are an important class of heterocyclic compounds, which mainly exist in various bioactive molecules and natural products. Isoquinoline compounds are also alkaloid compounds with important medicinal activities. So far, more than 1,000 kinds of isoquinoline alkaloids have been discovered, most of which are natural isoquinoline alkaloids have shown good biological activity, and they have been widely used in the fields of medicine and agriculture researches, such as antitumor, antihistamine, analgesic, and antibiotic, etc. In addition, some isoquinoline derivatives are useful ligands for the synthesis of phosphorescent emitters in organic light-emitting diodes (OLEDs). [0003] At present, there are many reports on the methods of synthes...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D217/02A61P35/00A61P29/00A61P31/00
CPCC07D217/02
Inventor 林伟胡秀秀蔡琦王雅珍韩健宋帅
Owner JIANGSU UNIV OF TECH
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