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Preparation method of 2-benzofuranone compound

A technology of benzofuranone and compounds, which is applied in the field of preparation of 3-benzofuranone compounds, can solve the problems of cumbersome operation and long reaction time, and achieve the effects of simple operation, short reaction time and mild reaction conditions

Active Publication Date: 2018-11-06
郯城县经开区医药发展有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0010] Utilize above-mentioned method to synthesize 3-benzofuranone compound, have certain shortcoming and deficiency: 1) need nitrogen protection; 2) operation is loaded down with trivial details; 3) reaction time is long

Method used

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  • Preparation method of 2-benzofuranone compound
  • Preparation method of 2-benzofuranone compound
  • Preparation method of 2-benzofuranone compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] Preparation of 3-benzofuranone compound 3a

[0024]

[0025] Add N-phenoxyacetamide (0.2mmol, 30mg), phenylpropionic acid (0.2mmol, 29mg), 5% rhodium catalyst, cobalt acetate hydrate, sodium pivaloate hydrate, methanol 1.0mL to 15mL thick In the wall pressure tube, stir for 12 hours at room temperature with an open opening. After the reaction, it was separated by column chromatography (200-300 mesh silica gel) (petroleum ether / ethyl acetate=4 / 1) to obtain N-(3-oxo-2-phenyl-2,3-dihydrobenzo Furan-2-yl)acetamide 3a (0.184mmol, 49mg), isolated yield 92%.

[0026] Spectral analysis data 3a:

[0027] 1 H NMR(500MHz, CDCl 3 ):δ7.69-7.68(m,2H),7.63-7.59(m,2H),7.37-7.36(m,2H),7.16(d,J=8.15Hz,1H), 7.07(t,J=7.35 Hz, 1H), 6.56 (s, 1H), 1.95 (s, 1H). 13 C NMR(125MHz, CDCl 3 ): δ194.7,170.0,169.4,137.8,134.4,129.7,128.9,125.6,125.1,122.3,119.8,112.2,91.5,22.3.HRMS(ESI-TOF,[M+Na] + ):calcd for C 16 H 13 NO 3 Na, 290.0793, found 290.0796.

Embodiment 2

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

[0030]

[0031] Spectral analysis data 3b:

[0032] 1 H NMR(500MHz, CDCl 3 ): δ7.70(brs,2H),7.44-7.38(m,5H), 7.08-7.07(m,2H), 6.96(brs,1H), 6.50(s,1H), 2.32(s,3H), 2.00(s,3H). 13 C NMR(125MHz, CDCl 3 ):δ194.9,169.8,167.8,138.9,134.6,132.0,129.6,128.9,125.6,124.6,119.6,111.9,91.7,22.4,20.6.HRMS(ESI-TOF,[M+Na] + ):calcd for C 17 H 15 NO 3 Na,304.0950,found 304.0951.

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] Spectral analysis data 3c:

[0037] 1 H NMR(500MHz, CDCl 3 ): δ7.71-7.69(m,2H), 7.52(d,J=7.8Hz,1H), 7.38-7.37(m,3H), 6.98(s,1H), 6.90(d,J=7.8Hz, 1H), 6.51(s, 1H), 2.43(s, 3H), 1.99(s, 3H). 13 C NMR(125MHz, CDCl 3 ):δ194.1,169.9,169.8,149.8,134.8,129.6,128.9,125.5,124.8,123.8,117.4,112.4,91.8,22.5,22.4.HRMS(ESI-TOF,[M+Na] + ):calcd for C 17 H 15 NO 3 Na,304.0950,found 304.0952.

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Abstract

The invention discloses a preparation method of a 3-benzofuranone compound and belongs to the technical field of organic synthesis. The method comprises the steps of adding a phenol derivative (0.2mmol, 30mg), phenylpropiolic acid (0.2mmol, 29mg), a 5% rhodium catalyst, a cobalt acetate hydrate, a sodium trimethylacetate hydrate, and 1.0mL methanol into a 15mL thick-wall pressure pipe, stirring for 12h at a room temperature with an orifice being opened, and after a reaction, performing silicagel column chromatographic separation to form a pure target product. The preparation method of the 3-benzofuranone compound has the characteristics that the method is scientific, reasonable, mild in condition, simple to operate, short in reaction time and the like. A reaction equation of the method isas follows as shown in the specification.

Description

Technical field [0001] The invention belongs to the technical field of organic synthesis, and specifically relates to a preparation method of 3-benzofuranone compounds. Background technique [0002] 3-benzofuranone compounds have good physiological activities. Such heterocyclic compounds and their derivatives can be used as antioxidants (J.Agric.Food Chem.2006,54,3551.), anti-B influenza virus (Eur. J. Med. Chem. 2013, 62, 534.), potent antibiotics for gram-positive pathogens (Chem. Eur. J. 2012, 18, 16123.) and antibacterial drugs (Bioorg. Med. Chem. Lett. 2012 , 22,6292.) In view of the wide biological activity and application value of 3-benzofuranone compounds, it is of great significance to develop a new method for the practical and effective synthesis of 3-benzofuranone compounds. [0003] The preparation methods of 3-benzofuranone compounds include: [0004] 1) Using o-chlorophenyldione and phenylboronic acid as raw materials [0005] Xu Minghua’s research group developed a ki...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D307/83
CPCC07D307/83
Inventor 李明袁文揆文丽荣张林宝
Owner 郯城县经开区医药发展有限公司
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