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Polysubstituted benzodihydrofuro heterocyclic compound and preparation method and application thereof

A benzodihydrofuran and heterocyclic technology is applied in the field of multi-substituted chromo-heterocyclic compounds and their preparation, which can solve the problems that do not conform to the development concept of green chemistry, have no application prospect, and have no substrate scope. Limited and other problems, to achieve the effect of novel and efficient synthesis method, wide substrate applicability and convenient operation

Active Publication Date: 2020-05-29
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] Although these strategies are diverse, there are still some limitations, such as harsh reaction conditions, high reaction temperature, limited substrate range, etc.
This makes the conversion efficiency of the reaction low, does not have broad application prospects, and does not conform to the development concept of green chemistry

Method used

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  • Polysubstituted benzodihydrofuro heterocyclic compound and preparation method and application thereof
  • Polysubstituted benzodihydrofuro heterocyclic compound and preparation method and application thereof
  • Polysubstituted benzodihydrofuro heterocyclic compound and preparation method and application thereof

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Experimental program
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Effect test

Embodiment 1

[0049] In the reaction tube, first add 0.03 mmol of palladium acetate, 0.5 mmol of copper chloride, 0.2 mmol of tetrabutylammonium bromide, 0.4 mmol of potassium carbonate, and finally add acetylene ketoxime ether (R 1 =R 2 =Ph) and 0.4 mmol of 1-iodo-2-(vinyloxy)benzene were dissolved in 2.5 ml of tetrahydrofuran solvent, stirred and reacted at 60 degrees Celsius at 700 rpm for 12 hours, and then stopped stirring. Add 5 mL of water, extract 3 times with ethyl acetate, combine the organic phases and use 0.5 g of anhydrous sodium sulfate to dry, filter, concentrate under reduced pressure, and then separate and purify by thin-layer chromatography to obtain the target product, the thin-layer chromatography used The developer is a mixed solvent of petroleum ether:ethyl acetate with a volume ratio of 150:1, and the yield is 81%.

[0050] The hydrogen spectrogram and the carbon spectrogram of the product obtained in this embodiment are respectively as follows figure 1 with figur...

Embodiment 2

[0058] In the reaction tube, first add 0.03 mmol of palladium acetate, 0.5 mmol of copper chloride, 0.2 mmol of tetrabutylammonium bromide, 0.4 mmol of potassium carbonate, and finally add acetylene ketoxime ether (R 1 = 4-methylphenyl, R 2 =Ph) and 0.4 mmol of 1-iodo-2-(vinyloxy)benzene were dissolved in 2.5 ml of tetrahydrofuran solvent, stirred and reacted at 60 degrees Celsius at 700 rpm for 12 hours, and then stopped stirring. Add 5 mL of water, extract 3 times with ethyl acetate, combine the organic phases and use 0.5 g of anhydrous sodium sulfate to dry, filter, concentrate under reduced pressure, and then separate and purify by thin-layer chromatography to obtain the target product, the thin-layer chromatography used The developer is petroleum ether:ethyl acetate mixed solvent with a volume ratio of 150:1, and the yield is 80%.

[0059] The hydrogen spectrogram and the carbon spectrogram of the product obtained in this embodiment are respectively as follows image 3 ...

Embodiment 3

[0067] In the reaction tube, first add 0.03 mmol of palladium acetate, 0.5 mmol of copper chloride, 0.2 mmol of tetrabutylammonium bromide, 0.4 mmol of potassium carbonate, and finally add acetylene ketoxime ether (R 1 = 4-chlorophenyl, R 2 =Ph) and 0.4 mmol of 1-iodo-2-(vinyloxy)benzene were dissolved in 2.5 ml of tetrahydrofuran solvent, stirred and reacted at 60 degrees Celsius at 700 rpm for 12 hours, and then stopped stirring. Add 5 mL of water, extract 3 times with ethyl acetate, combine the organic phases and use 0.5 g of anhydrous sodium sulfate to dry, filter, concentrate under reduced pressure, and then separate and purify by thin-layer chromatography to obtain the target product, the thin-layer chromatography used The developer is a mixed solvent of petroleum ether:ethyl acetate with a volume ratio of 100:1, and the yield is 84%.

[0068] The hydrogen spectrogram and the carbon spectrogram of the product obtained in this embodiment are respectively as follows Fig...

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Abstract

The invention belongs to the technical field of organic synthesis, and discloses a polysubstituted benzodihydrofuro heterocyclic compound and a preparation method and application thereof. The preparation method comprises the following steps: adding a palladium salt catalyst, an oxidizing agent, an additive and alkali into a reactor, performing dissolving into an organic solvent, performing stirring to react at 50-70 DEG C, and separating and purifying the reaction product to obtain the polysubstituted benzodihydrofuro heterocyclic compound, the reaction formula of the preparation method is shown as a formula (I). According to the method, the alkyne ketoxime ether and the o-iodophenyl alkenyl ether which are simple and easy to obtain are used as reaction raw materials to synthesize a seriesof polysubstituted benzodihydrofuro heterocyclic compounds, and the method has the characteristics of simple and easy-to-obtain raw materials, convenience in operation, mild conditions, high step economy, wide substrate applicability, good functional group tolerance and the like.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a multi-substituted benzodihydrofuranoheterocyclic compound and its preparation method and application. Background technique [0002] Heterocyclic compounds are important building blocks of many natural products, functional material molecules, agrochemicals, and pharmaceuticals. Among them, benzodihydrofuranoheterocyclic derivatives have attracted special attention due to their outstanding biological activities, for example (a) Prucalopride is a high-affinity 5-HT4 receptor agonist; (b) CellCept is an inosine monophosphate Dehydrogenase (IMPDH) inhibitors; (c) liliflol A and (d) cedralin A are selective COX-2 inhibitors. Its structural formula is as follows respectively: [0003] [0004] Therefore, it is necessary to explore efficient methods for the synthesis of benzodihydrofuranoheterocyclic compounds. In recent years, scientists have developed the ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D413/04C07D413/14
CPCC07D413/04C07D413/14
Inventor 伍婉卿周菲江焕峰
Owner SOUTH CHINA UNIV OF TECH
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