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Preparation method for sulfonyl hydroquinone compound

A technology for sulfonyl hydroquinone and compounds, which is applied in the field of preparation of sulfonyl hydroquinone compounds, to achieve the effect of simplifying the preparation process and increasing the yield

Active Publication Date: 2017-04-19
BIOCOMPOUNDS PHARMACEUTICAL INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Most of these synthetic methods undergo multi-step synthetic transformation, some use metal catalysts, and some use reagents such as sulfuryl chloride with poor stability, which have certain limitations in practical application.

Method used

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  • Preparation method for sulfonyl hydroquinone compound
  • Preparation method for sulfonyl hydroquinone compound
  • Preparation method for sulfonyl hydroquinone compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0062] Example 1 Preparation of 2-p-toluenesulfonyl-1,4-diphenol (3)

[0063]

[0064] A mixture of benzoquinone 1 (54 mg, 0.5 mmol), p-toluenesulfonyl hydrazide 2 (140 mg, 0.75 mmol) was dissolved in H 2 O (5.0 mL), the reaction mixture was reacted at room temperature for 12 hours, and the reaction was completed. The reaction was extracted three times with EtOAc, the combined organic phases were dried over anhydrous sodium sulfate, filtered, and the organic solvent was distilled off under reduced pressure. The residue was separated and purified by silica gel column chromatography to obtain 2-p-toluenesulfonyl-1,4-diphenol 3 with a yield of 67%. 1 H NMR (500MHz, CD 3 OD): δ7.83(d,J=6.8Hz,2H),7.40–7.29(m,3H),6.99–6.85(m,1H),6.74(dd,J=8.8,1.6Hz,1H),2.40 (s,3H). 13 C NMR (126MHz, CD 3 OD) δ149.94, 148.57, 144.18, 138.52, 129.00, 127.68, 126.08, 122.68, 118.19, 113.86, 20.11.

Embodiment 2

[0065] Example 2 Preparation of 2-benzenesulfonyl-1,4-diphenol (5)

[0066]

[0067] A mixture of benzoquinone 1 (54mg, 0.5mmol), benzenesulfonylhydrazide 4 (130mg, 0.75mmol) was dissolved in H 2 O (5.0 mL), the reaction mixture was reacted at room temperature for 12 hours, and the reaction was completed. The reaction was extracted three times with EtOAc, the combined organic phases were dried over anhydrous sodium sulfate, filtered, and the organic solvent was distilled off under reduced pressure. The residue was separated and purified by silica gel column chromatography to obtain 2-benzenesulfonyl-1,4-diphenol 5 with a yield of 65%. 1 H NMR (500MHz, CD 3 OD) δ7.96(d, J=7.9Hz, 2H), 7.61(t, J=7.4Hz, 1H), 7.53(t, J=7.6Hz, 2H), 7.40(d, J=2.8Hz, 1H ),6.95(dd,J=8.8,2.9Hz,1H),6.76(d,J=8.8Hz,1H). 13 C NMR (126MHz, CD 3 OD)δ149.95, 148.67, 141.41, 132.96, 128.48, 127.63, 125.83, 122.91, 118.24, 113.97.

Embodiment 3

[0068] Example 3 Preparation of 2-(2-bromobenzenesulfonyl)-1,4-diphenol (7)

[0069]

[0070] A mixture of benzoquinone 1 (54mg, 0.5mmol), 2-bromo-p-toluenesulfonylhydrazide 6 (190mg, 0.75mmol) was dissolved in H 2 O (5.0 mL), the reaction mixture was reacted at room temperature for 12 hours, and the reaction was completed. The reaction was extracted three times with EtOAc, the combined organic phases were dried over anhydrous sodium sulfate, filtered, and the organic solvent was distilled off under reduced pressure. The residue was separated and purified by silica gel column chromatography to obtain 2-(2-bromobenzenesulfonyl)-1,4-diphenol 7 with a yield of 60%. 1 H NMR (500MHz, CD 3 OD) δ8.36(d, J=7.9Hz, 1H), 7.71(d, J=7.9Hz, 1H), 7.60(t, J=7.6Hz, 1H), 7.50(dd, J=14.0, 6.9Hz ,1H),7.46(d,J=2.9Hz,1H),6.97(dd,J=8.8,2.9Hz,1H),6.72(d,J=8.8Hz,1H). 13 C NMR (126MHz, CD 3 OD)δ149.53, 148.76, 140.21, 134.81, 134.20, 132.18, 127.13, 124.38, 123.06, 119.94, 117.77, 115.83.

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Abstract

The invention belongs to the field of organic synthesis, and in particular, relates to a preparation method for a sulfonyl hydroquinone compound. According to the preparation method, a cheap and easily obtained quinone compound is used as a raw material, stable and easy-to-preserve sulfonyl hydrazide is used as a sulfonylation reagent, metal-free catalysis is adopted, reaction conditions are environmentally friendly, the preparation process is simplified, and the yield is increased.

Description

technical field [0001] The invention belongs to the field of organic synthesis, and in particular relates to a preparation method of sulfonyl hydroquinone compounds. Background technique [0002] Hydroquinones are a very important class of compounds, and they have broad application prospects in the fields of anti-oxidation, cosmetics, insecticides, photosensitization, and drug development. Among them, sulfonyl hydroquinone compounds, such as 2-sulfonyl-1,4-phenol or naphthol compounds, can exhibit strong antibacterial activity by inhibiting bacterial fatty acid biosynthesis (fatty acid condensing enzyme FabH enzyme). FabH enzyme inhibitors are expected to become broad-spectrum antibacterial drugs that selectively inhibit bacteria. The synthetic methods of sulfonyl hydroquinone reported in the literature mainly include: 1) using phenolic compounds as raw materials, using sulfonic acid or sulfonyl chloride as sulfonylation reagent, and obtaining the product with a medium yiel...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C315/00C07C317/22
CPCC07C315/00C07C317/22
Inventor 魏万国孙鹏康立涛李倩
Owner BIOCOMPOUNDS PHARMACEUTICAL INC
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