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4, 5-dyhydroxyl-3-H-spiro[furan-2, 3'-indole]-2'-ketone derivative as well as synthetic method and application thereof

A synthesis method and dihydroxyl technology, applied in the fields of botanical equipment and methods, applications, biocides, etc., can solve the problems of no research compound activity, limited reaction scope, complicated steps, etc., and achieve flexible reaction time and suitable for use. Wide-ranging, easy-to-use effects

Active Publication Date: 2014-05-21
海宁市袁花镇工业投资有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0010] These methods have the following disadvantages, (1) substrates, such as allyl silane and propargyl bromide, are more expensive and difficult to obtain; (2) the scope of reaction is not wide, and the steps are also more complicated; (3) there is no research on this method. activity of compounds

Method used

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  • 4, 5-dyhydroxyl-3-H-spiro[furan-2, 3'-indole]-2'-ketone derivative as well as synthetic method and application thereof
  • 4, 5-dyhydroxyl-3-H-spiro[furan-2, 3'-indole]-2'-ketone derivative as well as synthetic method and application thereof
  • 4, 5-dyhydroxyl-3-H-spiro[furan-2, 3'-indole]-2'-ketone derivative as well as synthetic method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040] Put isatin derivative (structure such as 1) (5.2g, 0.02mol), unsaturated ethyl cyanoacetate (structure such as 2a) (4.0g, 0.02mol), lithium hydroxide (0.092g) in a 100mL reaction flask , 0.004mol), 40mL toluene. The reaction mixture was stirred at 0°C for 10 hours, and then the solvent was removed under reduced pressure. The mixture of petroleum ether and ethyl acetate (volume ratio of petroleum ether to ethyl acetate was 10:1) was used as the eluent for column chromatography to obtain the structural formula as The 4,5-dihydroxy-3-H-spiro[furan-2,3'-indole]-2'-one derivative 3a of 3a (7.7 g, yield 83%).

[0041] The reaction equation is as follows:

[0042]

[0043] The structure of the 4,5-dihydroxy-3-H-spiro[furan-2,3'-indole]-2'-one derivative 3a obtained above was identified by nuclear magnetic resonance and high resolution mass spectrometry, 1 H NMR(400MHz, CDCl3)δ7.82(d,J=7.2Hz,1H), 7.52-7.44(m,2H), 7.44-7.36(m,4H), 7.19(t,J=7.3Hz,1H) ,6.84(d,J=7.8Hz,1H),6.04(s,1H),4...

Embodiment 2

[0045] Put isatin derivative (structure such as 1) (5.2g, 0.02mol), unsaturated ethyl cyanoacetate (structure such as 2a) (4.0g, 0.02mol), lithium hydroxide (0.092g) in a 100mL reaction flask , 0.004mol), 40mL water. The reaction mixture was stirred at 25°C for 10 hours, then ethyl acetate was added for extraction, dried, and the solvent was removed under reduced pressure. The mixture of petroleum ether and ethyl acetate (the volume ratio of petroleum ether to ethyl acetate was 10:1) was used as elution. Liquid was subjected to column chromatography to obtain 4,5-dihydroxy-3-H-spiro[furan-2,3'-indole]-2'-one derivative 3a (6.5g, yield 70%) with the structural formula 3a .

[0046] The reaction equation is as follows:

[0047]

[0048] The structure of the 5-chloro-4,5-dihydroxy-3-H-spiro[furan-2,3'-indole]-2'-one derivative 3a obtained above was identified by nuclear magnetic resonance and high resolution mass spectrometry , The results are the same as in Example 1. It is shown...

Embodiment 3

[0050] Put isatin derivative (structure such as 1) (5.2g, 0.02mol), unsaturated ethyl cyanoacetate (structure such as 2a) (4.0g, 0.02mol), lithium hydroxide (0.092g) in a 100mL reaction flask , 0.004mol), 40mL toluene. The reaction mixture was stirred at 25°C for 5 hours, and then the solvent was removed under reduced pressure. The mixture of petroleum ether and ethyl acetate (volume ratio of petroleum ether to ethyl acetate 10:1) was used as the eluent for column chromatography to obtain the structural formula as The 4,5-dihydroxy-3-H-spiro[furan-2,3'-indole]-2'-one derivative 3a of 3a (7.4g, yield 80%).

[0051] The reaction equation is as follows:

[0052]

[0053] The structure of the 5-chloro-4,5-dihydroxy-3-H-spiro[furan-2,3'-indole]-2'-one derivative 3a obtained above was identified by nuclear magnetic resonance and high resolution mass spectrometry , The results are the same as in Example 1. It is shown that the obtained 5-chloro-4,5-dihydroxy-3-H-spiro[furan-2,3'-indole...

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Abstract

The invention discloses a 4, 5-dyhydroxyl-3-H-spiro[furan-2, 3'-indole]-2'-ketone derivative as well as a synthetic method and an application thereof. The synthetic method comprises the following steps: in the presence of a solvent, carrying out a reaction on substituted or unsubstituted unsaturated nitrile ethyl acetate and an isatin derivative under catalysis of an alkali compound; and treating the reaction product to obtain the 4, 5-dyhydroxyl-3-H-spiro[furan-2, 3'-indole]-2'-ketone derivative. The method has the advantages that reaction time is agile, yield is high, operation is simple and convenient and the like, and is wide in application range and suitable for industrialized production. The 4, 5-dyhydroxyl-3-H-spiro[furan-2, 3'-indole]-2'-ketone derivative disclosed by the invention can be used as an antibacterial agent.

Description

Technical field [0001] The invention relates to the field of synthesis of heterocyclic compounds, in particular to a 4,5-dihydroxy-3-H-spiro[furan-2,3'-indole]-2'-one derivative, and a synthesis method and application thereof . Background technique [0002] Furan and its derivatives are an important class of heterocyclic compounds, which are widely found in natural products and have important biological activities. Many furan derivatives have antifungal, insecticidal and other physiological effects; more and more furan derivatives are used in the treatment of traumatic and ischemic central nervous system (CNS) injuries and diseases such as arteriosclerosis, liver disease, and cerebrovascular diseases. Very useful. Therefore, the synthesis of furan derivatives has broad application prospects. [0003] At the same time, indole is also a very important class of heterocyclic compounds. Its homologues or derivatives are widely found in nature and have a wide range of applications in ...

Claims

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Application Information

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IPC IPC(8): C07D491/107A01N43/90A01P3/00
CPCC07D491/107
Inventor 谢建武张雪
Owner 海宁市袁花镇工业投资有限公司
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