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Preparation method of 3-nitroso substituted indole derivative

A technology of indole derivatives and nitroso groups, which is applied in the field of preparation of indole derivatives, can solve problems such as cumbersome preparation process, and achieve the effects of simple preparation process, easy control and easy availability of raw materials

Active Publication Date: 2019-12-03
ZHENGZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] The purpose of the present invention is also to provide a preparation method of 3-nitroso substituted indole derivatives, to solve the problem that the existing preparation process is complicated

Method used

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  • Preparation method of 3-nitroso substituted indole derivative
  • Preparation method of 3-nitroso substituted indole derivative
  • Preparation method of 3-nitroso substituted indole derivative

Examples

Experimental program
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Embodiment 1

[0060] The preparation method of the 3-nitroso substituted indole derivatives of the present embodiment comprises the following steps: 0.1 mmol of N-methyl-N-nitrosoaniline, 0.15 mmol of benzoylsulfide ylide, dichloro(penta Add 0.005 mmol of methylcyclopentadienyl) rhodium (III) and 0.02 mmol of silver carbonate to a Shrek tube, dissolve in 1.0 mL of hexafluoroisopropanol solvent, react at 40°C for 9 hours, and then add to the reaction solution 0.25mmol of trifluoroacetic acid was added to the mixture, and the reaction was continued for 4h. The reaction solution was filtered through diatomaceous earth, the filtrate was concentrated, and purified by column chromatography to obtain 20.3 mg of the target product. The yield of the target product was 86%.

[0061] The 3-nitroso-substituted indole derivative obtained by the preparation method of this embodiment is 1-methyl-3-methylene-2-phenyl-1H-indole, and its structural formula is:

[0062]

Embodiment 2

[0064] The preparation process of the 3-nitroso-substituted indole derivatives of this embodiment refers to the process in Example 1, the only difference is that the benzoylthio ylide is replaced by 4-methoxybenzoylthio ylide, and the rest are the same. In this example, the reaction solution after the reaction was filtered through diatomaceous earth, the filtrate was concentrated, and purified by column chromatography to obtain 20 mg of the target product. The yield of the target product was 75%.

[0065] The 3-nitroso-substituted indole derivative obtained by the preparation method of this embodiment is 2-(4-methoxyphenyl)-1-methyl-3-nitroso-1H-indole, which The structural formula is:

[0066]

Embodiment 3

[0068] The preparation process of the 3-nitroso-substituted indole derivatives of this embodiment refers to the process in Example 1, the only difference is that the benzoyl sulfide ylide is replaced by 4-methylbenzoyl thio ylide, and the rest are same. In this example, the reaction solution after the reaction was filtered through diatomaceous earth, the filtrate was concentrated, and purified by column chromatography to obtain 20 mg of the target product. The yield of the target product was 80%.

[0069] The 3-nitroso-substituted indole derivative obtained by the preparation method of this embodiment is 1-methyl-3-nitroso-2-(p-tolyl)-1H-indole, and its structural formula is:

[0070]

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Abstract

The invention belongs to the technical field of organic synthesis and particularly relates to a preparation method of a 3-nitroso substituted indole derivative. The preparation method comprises the following steps: mixing N-nitrosoaniline as shown in a formula II, acyl sulfur ylide as shown in a formula III, a catalyst, silver salt and a solvent, performing carbon-hydrogen bond activation reaction, adding protonic acid and performing cyclizing and cascaded nitroso migration reaction, wherein the catalyst is a compound of transition metal and the transition metal is at least one of rhodium, ruthenium, cobalt, iridium and palladium. The structural formula of the 3-nitroso substituted indole derivative prepared by the preparation method is as shown in a formula I. By the preparation method provided by the invention, synthesis of the indole derivative can be realized by mixing the raw materials through a one-pot method, so the preparation process is simple and easy to control.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a preparation method of 3-nitroso substituted indole derivatives. Background technique [0002] Indole derivatives are an important class of heterocyclic compounds, which are widely used in the fields of medicine and chemical industry. Among them, 3-nitroso-substituted indole derivatives are an important class of organic synthesis intermediates, which can be used to prepare various high-spin organic polymers and LED polymers, and have good anti-inflammatory effects and can be used as DPP-IV inhibitors active pharmaceutical molecules. Based on the importance of 3-nitroso-substituted indole derivatives, their types and synthetic methods have also attracted extensive attention from researchers in related fields. The traditional Fischer indole synthesis method has been one of the most widely used methods, but this method has the problems of cumbersome steps, l...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D209/30
CPCC07D209/30
Inventor 崔秀灵吴迎涛皮超
Owner ZHENGZHOU UNIV
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