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A kind of polysubstituted 3-benzofuranone spirocyclohexene derivative and preparation method thereof

A technology of benzofuranone spirocyclohexene and benzofuranone is applied in the field of multi-substituted 3-benzofuranone spirocyclohexene derivatives and preparation thereof, and can solve the problems of limited types, 3-benzofuranone Due to the limited types of spiro compounds, the effect of low cost and good application prospects is achieved.

Active Publication Date: 2020-03-10
HENAN UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Based on the importance of 3-benzofuranone spirocyclic compounds in medicine and pesticides, chemists have developed a variety of methods for the construction of such compounds, but the preparation of 3-benzofuranone spirocyclic compounds reported in the literature The method mainly focuses on the construction of compounds such as 3-benzofuranone spirocyclopentane, 3-benzofuranone spirocyclopentane, and 3-benzofuranone spirocyclohexane, but the obtained 3-benzofuran The types of ketospirocyclic compounds are limited, and there are few reports on the 3-benzofuranone spirohexene derivatives widely existing in natural products, especially the multi-substituted 3-benzofuranone spirohexene derivatives, and limited variety

Method used

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  • A kind of polysubstituted 3-benzofuranone spirocyclohexene derivative and preparation method thereof
  • A kind of polysubstituted 3-benzofuranone spirocyclohexene derivative and preparation method thereof
  • A kind of polysubstituted 3-benzofuranone spirocyclohexene derivative and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] The structural formula of the multi-substituted 3-benzofuranone spirohexene derivative of the present embodiment is as follows:

[0025]

[0026] The preparation method of the turbine-shaped phthalazine derivatives of this embodiment is as follows: 20.1mg (0.15mmol) 3-benzofuranone, 31.8mg (0.3mmol) benzaldehyde, 19.8mg (0.3mmol) malononitrile, 8.3mg (40%eq) Potassium carbonate and 1mL of dichloromethane were added to the reaction test tube, stirred and reacted for 2h at 20-80°C, and separated by column chromatography to obtain the target product (eluent: petroleum ether and ethyl acetate volume ratio of 15:1 to 1:1).

Embodiment 2

[0028] The structural formula of the multi-substituted 3-benzofuranone spirohexene derivative of the present embodiment is as follows:

[0029]

[0030] The preparation method of the multi-substituted 3-benzofuranone spirocyclohexene derivative of this embodiment is as follows: 20.1mg (0.15mmol) 3-benzofuranone, 45.3mg (0.3mmol) 4-nitrobenzaldehyde, Add 19.8mg (0.3mmol) malononitrile, 8.3mg (40%eq) potassium carbonate, and 1mL of dichloromethane into the reaction test tube, stir and react for 5h at 20-80°C, and separate by column chromatography to obtain the target product (The eluent is: petroleum ether and ethyl acetate in a volume ratio of 15:1 to 1:1).

[0031] 1 H NMR (400MHz, CDCl 3 )δ7.51–7.35(m,4H),7.31–7.23(m,2H),7.23-7.03(m,7H),6.79(t,J=7.4Hz,1H),5.22(s,2H),4.34 (s,1H),3.98(s,1H).

Embodiment 3

[0033] The structural formula of the multi-substituted 3-benzofuranone spirohexene derivative of the present embodiment is as follows:

[0034]

[0035] The preparation method of the multi-substituted 3-benzofuranone spirocyclohexene derivative of this embodiment is as follows: 20.1mg (0.15mmol) 3-benzofuranone, 37.2mg (0.3mmol) 4-fluorobenzaldehyde, 19.8 mg (0.3mmol) malononitrile, 8.3mg (40%eq) potassium carbonate, and 1mL of dichloromethane were added to the reaction test tube, stirred and reacted for 72h at 20-80°C, and separated by column chromatography to obtain the target product ( The eluent is: petroleum ether and ethyl acetate in a volume ratio of 15:1 to 1:1).

[0036] 1 H NMR (400MHz, DMSO) δ7.71–7.56 (m, 3H), 7.40 (dd, J = 8.8, 5.3Hz, 2H), 7.21 (d, J = 8.4Hz, 1H), 7.17 (d, J = 7.7Hz, 1H), 7.11(t, J=8.4Hz, 2H), 6.91(t, J=7.4Hz, 3H), 4.98(s, 1H), 4.41(s, 1H), 3.40(s, 2H) .

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Abstract

The invention discloses a polysubstituted 3-benzofuranone spirocyclohexene derivative and a preparation method thereof. The structural formula of the polysubstituted 3-benzofuranone spirocyclohexene derivative is shown as Formula I shown in the description. The preparation method comprises the following steps: performing reaction on benzaldehyde, malononitrile and 3-benzofuranone for 1 to 72 hoursunder the condition of taking potassium carbonate as a catalyst, and dichloromethane as a solvent and adopting the temperature of 20 to 80 DEG C, and carrying out column chromatography isolation to obtain the polysubstituted 3-benzofuranone spirocyclohexene derivative. The invention provides the simple, efficient and convenient preparation method of the polysubstituted 3-benzofuranone spirocyclohexene derivative; the polysubstituted 3-benzofuranone spirocyclohexene derivative is prepared by taking the potassium carbonate as the catalyst and the dichloromethane as the solvent. The polysubstituted 3-benzofuranone spirocyclohexene derivative has the advantages of high efficiency, convenience, low cost, good application prospect 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 3-benzofuranone spirocyclohexene derivative and a preparation method thereof. Background technique [0002] 3-Benzofuranone spirocyclic compounds widely exist in nature, especially widely used in medicine, pesticides and other aspects. The 3-benzofuranone spirohexene derivative is closely related to people's life, and there are 3-benzofuranone spirohexene structural frameworks in many natural products and medicines, such as: isolated from marine fungi Natural product leptosphaerin c with antibacterial activity, antifungal antibiotic Griseofulvin, etc. Based on the importance of 3-benzofuranone spirocyclic compounds in medicine and pesticides, chemists have developed a variety of methods for the construction of such compounds, but the preparation of 3-benzofuranone spirocyclic compounds reported in the literature The method mainly focuse...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D307/94C07D409/14
CPCC07D307/94
Inventor 付记亚王彦波王建红谢亚撒丁涛袁金芳
Owner HENAN UNIVERSITY