A kind of preparation method and application of benzofuran-2,3-diketoxime derivative

A technology for benzofuran and derivatives, which is applied in the field of preparation of organic compounds, and can solve the problem of high equipment corrosion, great influence on operators, and difficulties in the source of raw materials for the synthesis route of benzofuran-2,3-diketoxime derivatives and other problems, to achieve the effects of short reaction time, low cost, and many types of product structures

Active Publication Date: 2019-01-08
江苏强盛功能化学股份有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The existing synthetic routes of benzofuran-2,3-diketoxime derivatives have difficult sources of raw materials, and the use of acetic acid as a solvent is highly corrosive to equipment and has a great impact on operators

Method used

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  • A kind of preparation method and application of benzofuran-2,3-diketoxime derivative
  • A kind of preparation method and application of benzofuran-2,3-diketoxime derivative
  • A kind of preparation method and application of benzofuran-2,3-diketoxime derivative

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] Example 1: Synthesis of 2-(hydroxyimino)-benzofuran-3(2H)-one

[0027] With 4-oxo-4H-benzopyran-3-carbaldehyde and sodium nitrite as raw materials, the reaction steps are as follows:

[0028] Add 4-oxo-4H-chromene-3-carbaldehyde (0.174 g, 1.0 mmol), sodium nitrite (0.069 g, 1.0 mmol), potassium persulfate (0.270 g, 1.0 mmol) and Acetone (4 ml), react at room temperature;

[0029] TLC tracking reaction until complete completion;

[0030] The crude product obtained after the reaction was separated by column chromatography (petroleum ether: ethyl acetate = 4:1) to obtain the target product (yield 61%). The analytical data of the product are as follows: 1 H NMR (400 MHz, DMSO- d 6 ): δ 12.45 (s, 1H),7.82 (t, J = 7.4 Hz, 1H), 7.75 (d, J = 7.5 Hz, 1H), 7.47 (d, J = 8.3 Hz, 1H), 7.33 (t, J = 7.5 Hz, 1H).

Embodiment 2

[0031] Example 2: Synthesis of 2-(hydroxyimino)-5-fluoro-benzofuran-3(2H)-one

[0032] Using 4-oxo-4H-6-fluorobenzopyran-3-carbaldehyde and sodium nitrite as raw materials, the reaction steps are as follows:

[0033] Add 4-oxo-4H-6-fluoro-benzopyran-3-carbaldehyde (0.192 g, 1.0 mmol), sodium nitrite (0.138 g, 2.0 mmol), potassium persulfate (0.59 g, 2.0 mmol) and acetone (4 ml), react at room temperature;

[0034] TLC tracking reaction until complete completion;

[0035] The crude product obtained after the reaction was separated by column chromatography (petroleum ether: ethyl acetate = 4:1) to obtain the target product (yield 83%). The analytical data of the product are as follows: 1 H NMR (400 MHz, DMSO- d 6 ): δ 12.52 (s, 1H), 7.68 (td, J = 9.0, 2.8 Hz, 1H), 7.58 (dd, J = 6.9, 2.8 Hz, 1H), 7.52 (dd, J=9.0, 3.7 Hz, 1H).

Embodiment 3

[0036] Example 3: Synthesis of 2-(hydroxyimino)-5-chloro-benzofuran-3(2H)-one

[0037] With 4-oxo-4H-6-chloro-benzopyran-3-carbaldehyde and sodium nitrite as raw materials, the reaction steps are as follows:

[0038] Add 4-oxo-4H-6-chloro-chromene-3-carbaldehyde (0.209 g, 1.0 mmol), sodium nitrite (0.207 g, 3.0 mmol), potassium persulfate (0.81 g, 3.0 mmol) and acetone (4 ml), react at room temperature;

[0039] TLC tracking reaction until complete completion;

[0040] The crude product obtained after the reaction was separated by column chromatography (petroleum ether: ethyl acetate = 4:1) to obtain the target product (yield 86%). The analytical data of the product are as follows: 1 H NMR (400 MHz, DMSO- d 6 ): δ 12.60 (s, 1H), 7.82 (dd, J = 8.8, 2.4 Hz, 1H), 7.76 (d, J = 2.2 Hz, 1H), 7.51 (d, J = 8.8Hz, 1H).

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Abstract

The invention discloses a preparing method and application for coumarone- 2, 3- diketone oxime derivative. The invention uses 3- formylchromone derivatives as the initiator and the raw materials are easy to get with multiple types and the industrial sodium nitrite as the reaction reagent at low cost; products obtained through the invention are diversified and can be widely applied in drug synthesis of bactericide, sanitizer, drugs for Alzheimer's disease treatment, drugs to restrain hepatitis C virus, SIRT1 and cancer cell proliferation in vitro, etc. In addition, for the method disclosed in the invention, reaction is performed in the air, namely room temperature reaction. The target product has high yield coefficient, low pollution, and simple reaction operation and post-processing, which is suitable for industrial production.

Description

technical field [0001] The invention belongs to the technical field of preparation of organic compounds, and in particular relates to a preparation method and application of benzofuran-2,3-diketoxime derivatives. Background technique [0002] In the past few decades, there have been few reports on benzofuran-2,3-diketoxime derivatives (see: Smith, L. I.; Holmes, R. R. J. Am. Chem. Soc. 1951 , 73, 4294-4297), its application value remains to be further developed. However, benzofuran-2,3-diketoxime derivatives can be easily converted into benzofuran-2,3-dione derivatives, which are widely used in various drugs, such as fungicides, disinfectants In the synthesis of drugs for treating Alzheimer's disease, drugs for inhibiting hepatitis C virus, drugs for inhibiting SIRT1 and proliferation of cancer cells in vitro. [0003] Benzofuran-2,3-dione derivatives can be used to prepare orange ketone derivatives: it has significant bactericidal effect; it has anticholinesterase activ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D307/83C07D307/86C07D405/06A61K31/343A61K31/4178A61K31/404A61K31/443A61P31/00A61P25/28A61P31/14A61P35/00A01N43/12A01N43/38A01N43/40A01N43/50A01P1/00A01P3/00
CPCA01N43/12A01N43/38A01N43/40A01N43/50C07D307/83C07D307/86C07D405/06
Inventor 应立曾润生周鹏骏孙网彬
Owner 江苏强盛功能化学股份有限公司
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