Synthetic method of indol norborneol alkanes and derivative thereof

A technology for norbornane and a synthesis method is applied in the field of synthesis of indolonorbornanes and derivatives thereof, and achieves the effects of simple synthesis method, broad application prospect and wide biological activity.

Inactive Publication Date: 2017-12-22
NANJING UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

So far, no reports have been found on the use of Catellani reaction

Method used

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  • Synthetic method of indol norborneol alkanes and derivative thereof
  • Synthetic method of indol norborneol alkanes and derivative thereof
  • Synthetic method of indol norborneol alkanes and derivative thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0032] Synthesis of N-acetylindolonorbornane

[0033] Dissolve indole in methanol solvent and mix evenly for reaction. After ten minutes, add iodine, potassium iodide, and sodium hydroxide, and react at room temperature for 3 hours. After 3 hours, monitor the end of the reaction by TLC. After distilling off the solvent, add acetyl chloride and tetrabutylsulfuric acid. Ammonium hydrogen and sodium hydroxide were dissolved in dichloromethane and mixed uniformly, stirred and reacted at room temperature for 3 hours, then the impurities were removed with a short silica gel column, and the solvent was evaporated to obtain a crude product, which was subjected to column chromatography (ethyl acetate:petroleum ether= 4:96) to obtain 3-iodo-N-acetylindole compound after separation. Dissolve 3-iodo-N-acetylindole compound, palladium acetate, tris(2-furyl)phosphine (TFP), norbornene and cesium carbonate in 1,4-dioxane solvent, mix well and place in React in a thick-walled pressure-resist...

Embodiment 2

[0035] Synthesis of 5-nitro-N-acetylindolonorbornane

[0036] Dissolve 5-nitroindole in methanol solvent and mix uniformly for reaction. Add iodine element, potassium iodide, and sodium hydroxide after ten minutes, and react at room temperature for 3 hours. After 3 hours, monitor the end of the reaction by TLC. After distilling off the solvent, add acetyl chloride, Tetrabutylammonium bisulfate and sodium hydroxide were dissolved in dichloromethane and mixed uniformly, stirred and reacted at room temperature for 3 hours, then removed impurities with a short silica gel column, evaporated the solvent to obtain a crude product, and the crude product was subjected to column chromatography (ethyl acetate : Petroleum ether=5:95) After separation, the 5-nitro-3-iodo-N-acetylindole compound was obtained. Dissolve 5-nitro-3-iodo-N-acetylindole compound, palladium acetate, tris(2-furyl)phosphine (TFP), norbornene, cesium carbonate in 1,4-dioxane solvent , mixed evenly and reacted in a t...

Embodiment 3

[0038] Synthesis of 5-Methyl-N-acetylindolonorbornane

[0039] Dissolve 5-methylindole in methanol solvent and mix uniformly for reaction. After ten minutes, add iodine, potassium iodide, and sodium hydroxide, and react at room temperature for 1 hour. After 1 hour, monitor the end of the reaction by TLC. After distilling off the solvent, add acetyl chloride, Tetrabutylammonium bisulfate and sodium hydroxide were dissolved in dichloromethane and mixed uniformly, stirred and reacted at room temperature for 24 hours, then removed impurities with a short silica gel column, evaporated the solvent to obtain a crude product, and the crude product was subjected to column chromatography (ethyl acetate : Petroleum ether=5:95) After separation, the 5-methyl-3-iodo-N-acetylindole compound was obtained. Dissolve 5-methyl-3-iodo-N-acetylindole compound, palladium acetate, TFP, norbornene, and cesium carbonate in 1,4-dioxane solvent, mix well and place in a thick-walled pressure-resistant tu...

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Abstract

The invention discloses a synthetic method of indol norborneol alkanes and a derivative thereof. The indol norborneol alkanes and the derivative thereof are shown as formula I in the description structurally. The synthetic method comprises the following steps: firstly taking an indol compound as a raw material, under the alkaline condition of sodium hydroxide, generating 3-iodine-N-acetyl indole or a derivative compound thereof through a reaction of indole or substituted indole and iodine and acetyl chloride, then under the condition of alkaline cesium carbonate in the 3-iodine-N-acetyl indole or the derivative compound therefore, using 1,4-dioxane as a solvent, using palladium acetate as a catalyst, using tri(2-furyl) phosphine as a ligand, and carrying out a heating reaction with norbornene to generate the indol norborneol alkanes and the derivative thereof. The preparation method is mild in condition and simple in operation, has relatively high atom economy, and the synthesized indol norborneol alkanes and derivative thereof are of relatively high potential value and wide application prospect in the field of medicinal chemistry.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis chemistry, and specifically relates to a method for synthesizing indolonorbornanes and derivatives thereof. Background technique [0002] Indole derivatives are an important class of compounds in nature and play an indispensable role in living organisms. Especially in recent years with the rapid development of biological science, indole derivatives are used in drugs and drug intermediates Occupying an important position, it has great development potential and broad application prospects in the fields of biochemistry, medicinal chemistry, and even material chemistry, and is widely used in the fields of medicine, pesticides, food and dye industries. Among them, the 2, 3-position disubstituted indole derivatives exhibit a wide range of biological activities in many natural and synthetic compounds. For example, the natural anticancer drug vinblastine (Vinblastine) can be used to treat lymph...

Claims

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Application Information

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IPC IPC(8): C07D209/94
CPCC07D209/94
Inventor 洪兴星姜超魏香宛赵彤
Owner NANJING UNIV OF SCI & TECH
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