Synthetic method of pyrano[2,3-c]carbazole compounds

A compound, 3-c technology, applied in the direction of organic chemistry, can solve the problems of unsatisfactory synthesis yield and narrow application range of substrates, etc.

Inactive Publication Date: 2016-02-03
CHENGDU KECHUANG JIASI TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0009] From the development context and technical performance of the prior art, it can be clearly seen that the synthesis methods of related analogues in the prior art have the disadvantages of narrow substrate application range and unsatisfactory synthesis yield.

Method used

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  • Synthetic method of pyrano[2,3-c]carbazole compounds
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  • Synthetic method of pyrano[2,3-c]carbazole compounds

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025]

[0026] Add 1mmol of the compound of formula (I), 3mmol of triphenylphosphine and 14g of solvent into the reaction kettle, stir and mix for 12min, then add 0.09mmol of catalyst and 0.05g of auxiliary agent, stir and react at 75°C for 7h, pour the mixture after the reaction is completed into cold water at 5°C, extracted with ethyl acetate, dried the organic phase with anhydrous sodium sulfate, filtered, rotary evaporated, and then separated through a silica gel column (n-hexane / ethyl acetate) to obtain the compound of formula (II), with a yield of 96.2%.

[0027] Wherein, the solvent is a mixture of DMF and tributylhexylphosphine bis(trifluoromethanesulfonyl)imide salt with a mass ratio of 8:1; the catalyst is nickel dichloride hexahydrate and paraiso Propyl calix[6]arene (CAS: 104789-79-9) mixture; additive is sodium lauroyl sarcosinate.

Embodiment 2

[0029]

[0030] Add 1mmol of the compound of formula (I), 3.2mmol of triphenylphosphine and 15g of solvent into the reaction kettle, stir and mix for 15min, then add 0.1mmol of catalyst and 0.06g of auxiliary agent, stir and react at 80°C for 6h, after the reaction is completed, the mixture Pour into cold water at 8°C, extract with ethyl acetate, dry the organic phase with anhydrous sodium sulfate, filter, rotary evaporate, and then separate through silica gel column (n-hexane / ethyl acetate) to obtain the compound of formula (II). was 95.7%.

[0031] Wherein, the solvent is a mixture of DMF and tributylhexylphosphine bis(trifluoromethanesulfonyl)imide salt with a mass ratio of 8:1; the catalyst is nickel dichloride hexahydrate and paraiso Propyl calix[6]arene (CAS: 104789-79-9) mixture; additive is sodium lauroyl sarcosinate.

Embodiment 3

[0033]

[0034] Add 1mmol of the compound of formula (I), 2.8mmol of triphenylphosphine and 12g of solvent to the reactor, stir and mix for 10min, then add 0.08mmol of catalyst and 0.04g of auxiliary agent, stir and react at 70°C for 8h, after the reaction is completed, the mixture Pour into cold water at 5°C, extract with ethyl acetate, dry the organic phase with anhydrous sodium sulfate, filter, rotary evaporate, and then separate through a silica gel column (n-hexane / ethyl acetate) to obtain the compound of formula (II). was 95.4%.

[0035] Wherein, the solvent is a mixture of DMF and tributylhexylphosphine bis(trifluoromethanesulfonyl)imide salt with a mass ratio of 8:1; the catalyst is nickel dichloride hexahydrate and paraiso Propyl calix[6]arene (CAS: 104789-79-9) mixture; additive is sodium lauroyl sarcosinate.

[0036] The present invention confirms and characterizes the structure of the target products of all examples and comparative examples, and the data are as...

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Abstract

The invention relates to a synthetic method of pyrano[2,3-c]carbazole compounds. According to the synthetic method, an efficient catalytic reaction system is creatively constructed from a novel substrate raw material, a compound solvent, a catalyst and an aid composition, so that the purpose of preparing a target product through one-step circularization is achieved; and furthermore, the synthetic method has the characteristics of mild reaction, rapidness and high efficiency and shows a wide application prospect.

Description

technical field [0001] The invention relates to a synthesis method of pyrano[2,3-c]carbazole compounds, belonging to the field of drug synthesis. Background technique [0002] Heterocyclic cyclized carbazoles have a wide range of pharmaceutical applications, such as anti-cancer, anti-inflammation, and anti-malarial, which makes the development of efficient synthesis methods for such compounds one of the key issues that researchers are concerned about. Pyranocarbazole compounds exist in a variety of plants in nature, and they are often used to treat different indications according to their medicinal effects. 7-MethoxyGlycomaurin, shown in the following structure, is a natural alkaloid isolated from the bark of the plant Glycosmis rupestris [see document PlantaMed., 1998, 64, 780], which has good pharmaceutical activity and excellent medicinal value. However, there is a lack of research reports on its synthesis method in the prior art. [0003] [0004] At present, there ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D491/052
CPCC07D491/052
Inventor 缪家戌
Owner CHENGDU KECHUANG JIASI TECH
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