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Method for synthesizing [b]-cyclized indole derivatives

An indole derivative, alkylation technology, applied in the direction of organic chemistry, etc., can solve problems such as compound instability, achieve the effect of green and simple method, avoid pre-activation, and high atom economy

Active Publication Date: 2021-04-16
NANJING UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the benzyne compound has a hydroxyl group at the end, and this compound is extremely unstable

Method used

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  • Method for synthesizing [b]-cyclized indole derivatives
  • Method for synthesizing [b]-cyclized indole derivatives
  • Method for synthesizing [b]-cyclized indole derivatives

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] Synthesis of 2,3,4,9-tetrahydro-1H-carbazole

[0035] Accurately weigh the 1H-indole reactant (0.2mmol, 23.4mg), transfer to the reaction vessel, add 1,4-dibromobutane (0.5mmol, 60μL), PdCl 2 (MeCN) 2 (10%mmol, 5.2mg), norbornene (0.6mmol, 56.5mg), potassium carbonate (0.4mmol, 55.3mg), add dropwise 1mLDMA and 9μL water in the thick-walled pressure-resistant tube, tighten the reaction tube stopper The reaction system was sealed, heated to 100°C, and reacted for 48 hours under the condition of stirring in an oil bath. After the reaction, the reaction solution was cooled to room temperature, filtered through short silica gel to remove insoluble impurities, extracted three times with ethyl acetate and water, and extracted once with brine, and the organic phase was removed from the solvent to obtain a crude product, which was separated by column chromatography (Eluent: ethyl acetate / petroleum ether=1:50), a pure and dry product was obtained with a yield of 45%. 1 H NMR (...

Embodiment 2

[0037] Synthesis of 6-nitro-2,3,4,9-tetrahydro-1H-carbazole

[0038] Accurately weigh 5-nitro-1H-indole reactant (0.2mmol, 32.4mg), transfer to reaction vessel, add 1,4-dibromobutane (0.5mmol, 60μL), PdCl 2 (MeCN) 2 (10%mmol, 5.2mg), norbornene (0.6mmol, 56.5mg), potassium carbonate (0.4mmol, 55.3mg), add dropwise 1mLDMA and 9μL water in the thick-walled pressure-resistant tube, tighten the reaction tube stopper The reaction system was sealed, heated to 80°C, and reacted for 36 hours under the condition of stirring in an oil bath. After the reaction, the reaction solution was cooled to room temperature, filtered through short silica gel to remove insoluble impurities, extracted three times with ethyl acetate and water, and extracted once with brine, and the organic phase was removed from the solvent to obtain a crude product, which was separated by column chromatography (Eluent: ethyl acetate / petroleum ether=1:20), a pure and dry product was obtained with a yield of 82%. 1 ...

Embodiment 3

[0040] Synthesis of 6-carbonitrile-2,3,4,9-tetrahydro-1H-carbazole

[0041] Accurately weigh 5-methyl-1H-indole reactant (0.2mmol, 28.4mg), transfer to reaction vessel, add 1,4-dibromobutane (0.5mmol, 60μL), PdCl 2 (MeCN) 2 (10%mmol, 5.2mg), norbornene (0.6mmol, 56.5mg), potassium carbonate (0.4mmol, 55.3mg), add dropwise 1mLDMA and 9μL water in the thick-walled pressure-resistant tube, tighten the reaction tube stopper The reaction system was sealed, heated to 100°C, and reacted for 36 hours under the condition of stirring in an oil bath. After the reaction, the reaction solution was cooled to room temperature, filtered through short silica gel to remove insoluble impurities, extracted three times with ethyl acetate and water, and extracted once with brine, and the organic phase was removed from the solvent to obtain a crude product, which was separated by column chromatography (Eluent: ethyl acetate / petroleum ether=1:50), a pure and dry product was obtained with a yield of...

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Abstract

The invention discloses a method for synthesizing [b]-cyclized indole compounds. The steps are: under the action of a palladium catalyst, norbornene is used as a transient guiding medium, and a dihaloalkane is used as an alkylating agent, Under the action of alkali, the domino reaction of indole C2, C3 alkylation and ring closure is realized in one pot, and [b]-cyclized indole compounds are effectively synthesized. The method has mild conditions, directly uses commercially available indole as the substrate, saves the pre-functionalization process, reduces the reaction steps, has high atom economy, and modifies the simple indole small molecule structure, [ b]‑cyclized indole derivatives can be further used in medicine or total synthesis research, and have high potential value and broad application prospects in medicinal chemistry and other fields.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis chemistry, and specifically relates to a method for synthesizing [b]-cyclized indole derivatives. Background technique [0002] Many biologically active natural and unnatural compounds contain indole skeletons. For example, indole alkaloids account for a quarter of the numerous alkaloid compounds. Indole compounds, as an important class of organic compounds, are widely used in the fields of medicine, pesticides, food, feed additives and dye industries. [0003] The core structure of [b]-cyclized indole exists in many biologically active indole derivatives such as tyrosine kinases and alkaloids. To date, many works have been carried out to build six-membered rings on indoles. The most commonly used method is the Fischer indole synthesis, a commonly used method for the synthesis of indole ring systems, discovered by Hermann Emil Fischer in 1883. The reaction is to use phenylhydrazine, ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D209/86C07D209/88C07D209/94
CPCC07D209/86C07D209/88C07D209/94
Inventor 姜超李建华高亚东
Owner NANJING UNIV OF SCI & TECH
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