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A kind of preparation method of 2-aminobenzofuran compound

A compound, aminobenzene technology, applied in the field of preparation of 2-aminobenzofuran compounds, can solve the problems of large environmental pollution of raw materials, low atom economy, complicated steps and the like, and achieves easy purification treatment, high yield, and synthesis method. simple effect

Active Publication Date: 2022-03-08
QINGDAO UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0009] However, the above-mentioned method for preparing 2-aminobenzofuran has certain shortcomings and deficiencies: 1) the steps are cumbersome and the efficiency is low; 2) the raw materials used are more polluting to the environment; 3) the atom economy is low

Method used

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  • A kind of preparation method of 2-aminobenzofuran compound
  • A kind of preparation method of 2-aminobenzofuran compound
  • A kind of preparation method of 2-aminobenzofuran compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] Preparation of 2-aminobenzofuran compound 3a

[0024]

[0025] To a 25ml test tube was added N-phenoxyacetamide 1a (0.2mmol, 30.2mg), 2 (0.26mmol, 111.3mg) and tetrabutylammonium fluoride (0.26mmol, 67.8mg). Tetrahydrofuran (2 mL) was added, stirred at -30°C, and reacted for 2 hours. After the reaction is complete, use a rotary evaporator to remove the solvent to obtain a crude product, which is separated by column chromatography (200-300 mesh silica gel) (petroleum ether / ethyl acetate=4 / 1), and use a rotary evaporator to remove the solvent to obtain the product The yield of 2-aminobenzofuran compound 3a is 92%.

[0026] Spectral analysis data 3a:

[0027] 1 H NMR (500MHz, DMSO-d 6 )δ11.25(s,1H),7.49(d,J=6.8Hz,1H),7.45(d,J=7.6Hz,1H),7.17(p,J=7.3Hz,2H),6.63(s, 1H), 2.11(s, 3H). 13 C NMR (125MHz, DMSO-d 6 )167.59,149.86,149.20,129.59,123.53,122.78,120.24,110.47,88.93,23.59.HRMS(ESI)m / z calcd for C 10 h 9 NO 2 (M+Na) + :198.0531,found 198.0532.

Embodiment 2

[0029] Replace 1a in Example 1 with 1b, and other conditions are the same as Example 1. The experimental results are shown in Table 1.

[0030]

[0031] Spectrum analysis data 3b:

[0032] 1 H NMR (500MHz, DMSO-d 6 )δ11.18(s,1H),7.31(d,J=8.3Hz,1H),7.27(s,1H),6.97(d,J=8.3Hz,1H),6.55(s,1H),2.35( s,3H),2.10(s,3H). 13 C NMR (125MHz, DMSO-d 6 )δ167.48,149.91,147.56,132.37,129.67,123.72,120.15,109.99,88.77,23.57,21.37.HRMS(ESI)m / z calcd for C 11 h 11 NO 2 (M+Na) + :212.0687, found 212.0690.

Embodiment 3

[0034] Replace 1a in Example 1 with 1c, and other conditions are the same as Example 1. The experimental results are shown in Table 1.

[0035]

[0036] Spectrum analysis data 3c:

[0037] 1 H NMR (500MHz, DMSO-d 6 )δ11.33(s,1H),7.46(dd,J=8.8,4.2Hz,1H),7.30(dd,J=9.1,2.6Hz,1H),6.97(td,J=9.3,2.7Hz,1H ),6.64(s,1H),2.12(s,3H). 13 C NMR (125MHz, DMSO-d 6 )δ167.71,160.23,158.35,151.57,145.46,130.96,111.46,109.82,109.61,106.11,105.91,89.19,23.60.HRMS(ESI)m / z calcd for C 10 h 8 NO 2 F(M+Na) + :216.0437, found 216.0439.

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Abstract

The invention discloses a preparation method of a novel 2-aminobenzofuran compound belonging to the technical field of organic synthesis. The method is: at -30°C, add substituted N-phenoxyamide and 1-[[(triisopropyl)silyl]ethynyl]-1,2-phenyliodide to the reactor ‑3(1H)‑ketone and tetrabutylammonium fluoride, after stirring and reacting in a solvent, use a rotary evaporator to concentrate to obtain a crude product, which is separated by silica gel column chromatography to obtain the target product. The synthesis method of the 2-aminobenzofuran compound provided by the present invention has the characteristics of scientific rationality, relatively simple synthesis method, high yield of the target compound, easy purification and treatment of the product, and the like. Its reaction equation is as follows:

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a preparation method of 2-aminobenzofuran compound. Background technique [0002] Benzofuran compound is a heterocyclic compound, its structure is benzene as the core, combined with furan ring. Among them, 2-aminobenzofuran is a class of highly active compounds that exist in some natural products and medicines and have important biological activities. Such as antibacterial activity, analgesic activity, antifungal and viral activity. (Bioorg. Med. Chem. 2005, 13, 6629.) [0003] In view of the wide biological activity and application value of 2-aminobenzofuran, it is of great significance to develop a new method for the practical and effective synthesis of 2-aminobenzofuran. [0004] In recent years, the methods for preparing 2-aminobenzofuran include: [0005] 1) In 2010, Saku's research group developed a 2-aminobenzofuran compound starting from o-hydrox...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D307/82
Inventor 李明王嘉辉李卫文丽荣
Owner QINGDAO UNIV OF SCI & TECH