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Preparation method of compound containing benzofuran structure

A technology for benzofuran and compound is applied in the field of preparation of compounds containing benzofuran structure, can solve the problems of low yield, high price, serious environmental pollution of reaction reagents and the like, and achieves the effects of high yield and mild conditions

Active Publication Date: 2015-03-04
GUANGZHOU CHEM CO LTD CHINESE ACADEMY OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

There are some deficiencies in the above methods, such as the use of expensive catalysts, serious environmental pollution of reaction reagents and low yields, etc.

Method used

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  • Preparation method of compound containing benzofuran structure
  • Preparation method of compound containing benzofuran structure
  • Preparation method of compound containing benzofuran structure

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0021] The preparation of 2-amino-3-cyanobenzofuran-5-carboxylic acid methyl ester comprises the following steps:

[0022] Add methyl 3-dehydroshikimate (0.37g, 2mmol), malononitrile (0.13g, 2mmol) and distilled water (10ml) into a 50ml two-necked flask equipped with a thermometer and a reflux condenser, and slowly heat up to 90°C , stirred for about 4 hours, a large amount of white solids were precipitated, and the reaction was detected by TLC. After the reaction was completed, it was cooled and filtered, and the solids were recrystallized with ethyl acetate to obtain white needle-like crystals of 2-amino-3-cyanobenzofuran-5- Methyl carboxylate 0.42g, yield 97%.

[0023] Compound characterization data are as follows: m.p.>200℃. 1 H NMR (400MHz, DMSO-d 6 ), δ: 8.50 (s, 2H, -NH 2 ), 7.74 (d, 1H, J=1.6Hz, 4-ArH), 7.70 (dd, 1H, J 1 =8.4Hz,J 2 = 1.6Hz, 6-ArH), 7.48(d, 1H, J=8.4Hz, 7-ArH), 3.86(s, 3H, -OCH 3 ); 13 C NMR (100MHz, DMSO-d 6 ), δ: 52.2, 60.1, 110.0, 114.7, 116....

Embodiment 2

[0026] The preparation of 2-amino-3-cyanobenzofuran-5-carboxylic acid methyl ester comprises the following steps:

[0027] Add methyl 3-dehydroshikimate (0.37g, 2mmol), malononitrile (0.20g, 3mmol) and distilled water (10ml) into a 50ml two-necked flask equipped with a thermometer and a reflux condenser, and slowly heat up to 100°C , stirred for about 3 hours, a large amount of white solids were precipitated, and the reaction was detected by TLC. After the reaction was completed, it was cooled and filtered, and the solid was recrystallized with ethyl acetate to obtain white needle-like crystals of 2-amino-3-cyanobenzofuran-5- Methyl carboxylate 0.41g, yield 95%.

[0028] Compound characterization data are as follows: m.p.>200℃. 1 H NMR (400MHz, DMSO-d 6 ), δ: 8.50 (s, 2H, -NH 2 ), 7.74 (d, 1H, J=1.6Hz, 4-ArH), 7.70 (dd, 1H, J 1 =8.4Hz,J 2 = 1.6Hz, 6-ArH), 7.48(d, 1H, J=8.4Hz, 7-ArH), 3.86(s, 3H, -OCH 3 ); 13 C NMR (100MHz, DMSO-d 6 ), δ: 52.2, 60.1, 110.0, 114.7, 116.6...

Embodiment 3

[0031] The preparation of 2-amino-3-cyanobenzofuran-5-carboxylic acid methyl ester comprises the following steps:

[0032] Add methyl 3-dehydroshikimate (0.37g, 2mmol), malononitrile (0.15g, 2.2mmol) and ethanol (10ml) into a 50ml two-necked flask equipped with a thermometer and a reflux condenser, and reflux for about 3h. The reaction was detected by TLC. After the reaction was completed, it was cooled, and the solvent was removed by rotary evaporation. The solid was recrystallized from ethyl acetate to obtain 0.38 g of white needle-like crystals, with a yield of 89%.

[0033] Compound characterization data are as follows: m.p.>200℃. 1 H NMR (400MHz, DMSO-d 6 ), δ: 8.50 (s, 2H, -NH 2 ), 7.74 (d, 1H, J=1.6Hz, 4-ArH), 7.70 (dd, 1H, J 1 =8.4Hz,J 2 = 1.6Hz, 6-ArH), 7.48(d, 1H, J=8.4Hz, 7-ArH), 3.86(s, 3H, -OCH 3 ); 13 C NMR (100MHz, DMSO-d 6 ), δ: 52.2, 60.1, 110.0, 114.7, 116.6, 123.2, 125.8, 128.7, 150.5, 166.0, 166.6; IR(KBr), v / cm -1 :3409,3320,2950,2212,1718,1646,158...

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Abstract

The invention belongs to the technical field of chemical synthesis and discloses a preparation method of a compound containing a benzofuran structure. According to the preparation method, 3-methyl dehydroshikimate and a cyano-containing methylene compound are adopted as raw materials and reacted in the presence of a solvent and a catalyst to obtain the compound containing the benzofuran structure. The raw material 3-methyl dehydroshikimate, which is used in the invention, is prepared from renewable and non-food biomass resource shikimic acid as a raw material having Chinese characteristics by virtue of a simple and convenient method, therefore, the synthesis method is completely in line with the basic concept of modern green chemistry and the sustainable development of benzofuran compounds can be achieved.

Description

technical field [0001] The invention belongs to the technical field of chemical synthesis, and in particular relates to a preparation method of a compound containing a benzofuran structure. Background technique [0002] Benzofuran is an important structural nucleus, and related structure types are widely found in natural products and important biologically active molecules. For example: compound A (Ailanthoidol) is a natural product extracted from plants of the genus Zanthoxylum, which has antiviral, antifungal and antioxidative activities; compound B is a class of H3 receptor agonist and has anti-senile dementia activity . All of the above biologically active molecules have the structural core of benzofuran. [0003] [0004] At present, the synthetic method of benzofuran compound mainly contains: (1) coupling reaction (J.Am.Chem.Soc., 2005,127:15022-15023; Org. Lett.,2008,10:4211-4214); (2) Copper (I) catalyzed the coupling reaction of acetylene compounds (Org.Lett.,...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D307/84
CPCC07D307/84
Inventor 张恩生邹永徐田龙王德建陈爱民魏文
Owner GUANGZHOU CHEM CO LTD CHINESE ACADEMY OF SCI
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