Dibenzofuran acrylate compound and preparation method therefor

A technology of furan acrylates and compounds, which is applied in the field of dibenzofuran acrylate compounds and their preparation, can solve problems such as the inability to meet the needs of direct synthesis of structurally diverse multifunctional group dibenzofuran derivatives, and achieve substrate application The effect of wide range of properties, high reaction yield, and simple and easy synthetic method

Active Publication Date: 2019-09-20
ZHEJIANG UNIV CITY COLLEGE
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Therefore, the above two types of synthetic strategies cannot meet the demand for direct synthesis of structurally diverse and multifunctional dibenzofuran derivatives.

Method used

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  • Dibenzofuran acrylate compound and preparation method therefor
  • Dibenzofuran acrylate compound and preparation method therefor
  • Dibenzofuran acrylate compound and preparation method therefor

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0065] Example 1: Dimethyl(Z)-8-chloro-1-(1,4-dimethoxy-1,4-dioxobut-2-en-2-yl)-4-(p-toluene Yl)dibenzo[b,d]furan-2,3-dicarboxylic acid

[0066]

[0067] Combine (E)-4-chloro-2-(2-nitroalkene)phenol (1.0mmol, 1.0 equivalent) and 2-(dimethyl-λ 4 -Sulfylene)-1-(p-tolyl)ethane-1-one (1.0 mmol, 1.0 equivalent) was dissolved in 8 mL of acetonitrile, and stirred at 35°C for half an hour. Then, dimethyl dimethylate (2.1 mmol, 2.1 equivalent) and potassium carbonate (1.0 mmol, 1.0 equivalent) were added to the above system, and stirring was continued for 12 hours at 35°C. After the reaction was completed, the reaction system was diluted with 20 mL of ethyl acetate. Then it was washed once with 5 mL of water, separated into the ethyl acetate layer and concentrated under reduced pressure. The obtained crude product was separated and purified by silica gel column chromatography (petroleum ether: ethyl acetate = 7:1) to obtain a white powder with a yield of 78%.

[0068] White solid, yield ...

Embodiment 2

[0082] Example 2: Dimethyl (Z)-8-chloro-1-(1,4-dimethoxy-1,4-dioxobut-2-en-2-yl)-4-phenyldi Benzo[b,d]furan-2,3-dicarboxylic acid

[0083]

[0084] The synthesis steps are the same as in Example 1, except that 2-(dimethyl-λ 4 -Sulfylene)-1-(p-tolyl)ethane-1-one replaced with 2-(dimethyl-λ 4 -Sulfylene)-1-phenylethane-1-one to obtain a white solid with a yield of 74%.

[0085] White solid, yield 74%. Melting point: 115.1-116.2°C. 1 H NMR(500MHz, CDCl 3 )δ8.10(d,J=2.2Hz,1H), 7.53-7.48(m,5H), 7.484-7.473(m,2H), 6.43(s,1H), 3.96(s,3H), 3.88(s , 3H), 3.79 (s, 3H), 3.62 (s, 3H). 13 C NMR(125MHz, CDCl 3 )δ167.93,166.50,165.78,164.82,155.71,154.93,137.36,133.66,132.76,130.78,130.16,129.46,129.40,128.94,128.85,128.50,125.97,125.55,124.15,123.66,122.93,113.28,53.00,52.72. ,52.62. HRMS(ESI):m / z calcd for[2M+Na] + :1095.1640,found:1095.1639.

Embodiment 3

[0086] Example 3: Dimethyl (Z)-8-chloro-1-(1,4-dimethoxy-1,4-dioxobut-2-en-2-yl)-4-(3- Methoxyphenyl) dibenzo[b,d]furan-2,3-dicarboxylic acid

[0087]

[0088] The synthesis steps are the same as in Example 1, except that 2-(dimethyl-λ 4 -Sulfylene)-1-(p-tolyl)ethane-1-one replaced with 2-(dimethyl-λ 4 -Sulfylene)-1-(3-methoxyphenyl)ethane-1-one to obtain a white solid with a yield of 76%.

[0089] White solid, yield 76%. Melting point: 139.8-141.4°C. 1 H NMR(500MHz, CDCl 3 )δ8.10(d,J=1.2Hz,1H),7.48(dd,J=7.2,5.1Hz,2H),7.42(t,J=7.9Hz,1H),7.11–6.99(m,3H), 6.42 (s, 1H), 3.96 (s, 3H), 3.88 (s, 3H), 3.85 (s, 3H), 3.78 (s, 3H), 3.65 (s, 3H). 13 C NMR(125MHz, CDCl 3 )δ167.91,166.46,165.76,164.79,159.48,155.70,154.86,137.35,133.97,133.61,130.78,130.19,129.57,129.41,128.95,125.79,125.54,124.13,123.68,122.92,121.83,115.01,114.55.36,113. ,52.98,52.80,52.70,52.68.HRMS(ESI):m / z calcd for[2M+Na] + :1155.1852,found:1155.1856.

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Abstract

The invention discloses a dibenzofuran acrylate compound and a preparation method therefor. The dibenzofuran acrylate compound has a structural formula represented by a formula shown in the description, wherein R1 is H, halogen, alkoxy, nitro or an ester group, R2 is various substituted phenyl, naphthyl, alkyl or heterocyclic aryl, R3 is H, methyl ester or ethyl ester, and R4 is methyl or ethyl. The invention further simultaneously discloses the preparation method for the dibenzofuran acrylate compound. The method comprises the step of subjecting a (E)-2-(2-nitro)phenol derivative, sulfur ylide and propiolate to a [4+1]/[3+2] aromatic cyclization reaction in the presence of a corresponding base at a certain temperature, thereby synthesizing the polyfunctionalized dibenzofuran acrylate compound. The preparation method provided by the invention has the advantages that the operation is simple, the raw materials are readily available, functional groups of reaction are good in tolerance, a plurality of substituents can be simultaneously introduced, the product is easy to separate, and the like.

Description

Technical field [0001] The invention belongs to a compound synthesis method, and mainly relates to a dibenzofuran acrylate compound and a preparation method thereof. Background technique [0002] Dibenzofuran derivatives are a very important class of small organic molecular compounds. Because of their unique biological and chemical properties, they are widely used in natural products, medicines, and materials science. In fact, many functional small molecule compounds contain dibenzofuran structures in their structural frameworks: such as phytoantitoxin γ-Cotonefuran (J.Org.Chem.2012,8,613), anti-inflammatory agent Furobufen (Can.J.Physiol) .Pharmacol.1974,52,669), tyrosine kinase inhibitor Fortuneanoside L (Int.J.Mol.Sci.2015,16,28598) and functional fragments of organic fluorescent light-emitting diodes (PhOLEDs) (ACS Appl.Mater.Interfaces 2016) ,8,16186), the structural formula is as follows: [0003] [0004] At present, there are two main strategies for the synthesis of diben...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D307/91
CPCC07D307/91
Inventor 邵加安
Owner ZHEJIANG UNIV CITY COLLEGE
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