A kind of method for synthesizing furoxan compound

A technology for oxidizing furoxan and compounds, which is applied in the field of synthesizing furoxan oxide compounds, can solve the problems of narrow application range, low yield and high cost, and achieves the effects of wide application scope, low price and low cost

Active Publication Date: 2016-08-17
CHENGDU LIKAI CHIRAL TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The purpose of the present invention is to provide a method for synthesizing furoxan compounds to solve the above-mentioned problems of narrow application range, high cost, low yield and environmental protection

Method used

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  • A kind of method for synthesizing furoxan compound
  • A kind of method for synthesizing furoxan compound
  • A kind of method for synthesizing furoxan compound

Examples

Experimental program
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Effect test

Embodiment 1

[0031] Example 1 Synthesis of 3-methyl-4-phenylfuroxan

[0032] The synthesis method is: put a magnetic stirrer in a hard glass tube, weigh 38.8 mg (0.2 mmol) of 2-nitro-phenylpropyl-1-ketoxime and 47.6 mg (0.25 mg) of p-toluenesulfonyl chloride in sequence. mmol). Place the reaction tube under an ice bath, add 6 mL of mesitylene solvent, and finally add triethylenediamine hexahydrate (DABCO·6H 2 O) 44mg (0.2mmol), the reaction was continued to stir in ice bath for 20min, separated and purified to obtain 34mg of colorless crystals, yield 95%.

Embodiment 2

[0033] Example 2 Synthesis of 3-methyl-4-phenylfuroxan

[0034] The synthesis method is: put a magnetic stirrer in a hard glass tube, weigh 38.8 mg (0.2 mmol) of 2-nitro-phenylpropyl-1-ketoxime and 47.6 mg (0.25 mg) of p-toluenesulfonyl chloride in sequence. mmol). Place the reaction tube under an ice bath, add 6 mL of mesitylene solvent, and finally add 51.7 mg (0.4 mmol) of isopropylethylamine, and continue to stir the reaction at 50°C for 15 min. Separate and purify to obtain 28 mg of colorless crystals. rate of 68%.

Embodiment 3

[0035] Example 3 Synthesis of 3-methyl-4-phenylfuroxan

[0036] The synthesis method is: put a magnetic stirrer in a hard glass tube, weigh 38.8 mg (0.2 mmol) of 2-nitro-phenylpropyl-1-ketoxime and 76.16 mg (0.4 mg) of p-toluenesulfonyl chloride in sequence mmol). Place the reaction tube under an ice bath, add 6 mL of chloroform solvent, and finally add triethylenediamine hexahydrate (DABCO·6H 2 O) 44mg (0.2mmol), the reaction was continued to stir at 0°C for 20min, separated and purified to obtain 27mg of colorless crystals, with a yield of 75%.

[0037] The colorless crystals obtained in Examples 1-3 have the same structural identification data, specifically as follows: m.p.94.3-95.1°C; 1 H NMR (300MHz, CDCl 3 ), δ(ppm):2.35(s,3H),7.52-7.55(m,3H),7.66-7.69(m,2H); 13 C NMR (75MHz, CDCl 3), δ (ppm): 9.1, 112.1, 126.7, 127.4, 129.2, 131.0, 156.8. HRMS (ESI) Calcd.for C 9 h 8 N 2 o 2 [M+Na] + :199.0478; found: 199.0483, it can be concluded that its structure is:

[00...

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Abstract

The invention discloses a novel synthesis method of furoxan, and belongs to the fields of organic chemistry and medicine. The synthesis method comprises the following steps: weighing alpha-nitroxime and sulfonyl chloride, adding the weighed alpha-nitroxime and sulfonyl chloride into a solvent, placing the mixture into a reactor, carrying out reactions at a temperature of -10 to 50 DEG C under stirring, adding alkali, keeping on stirring, and finally carrying out separation and purification after the reactions completely finish, so as to obtain the furoxan. The reaction conditions are mild, asymmetrical furoxan compounds with different substituents can be obtained, the application range of the method is wide, the price of the raw material sulfonyl chloride is lower than that of NCS, the whole reaction period is short and lasts about 20 minutes, the cost is low, the yield can reach 95% or more and is higher than that of methods which have been reported before, moreover, no pollutant is discharged, and thus the method is environment-friendly.

Description

technical field [0001] The invention relates to the fields of organic chemistry and medicine, in particular to a method for synthesizing furoxan compounds. Background technique [0002] Oxyfurazan compounds are an important class of heterocyclic compounds, which are widely used in the field of medicine. Studies have shown that oxyfurazan compounds can release NO transmitters in vivo and activate guanylate cyclase, and these compounds also have bactericidal, anti-tumor, anti-inflammatory activities and improve cardiovascular function. For example: 3-cyano-4-phenylfuroxan can release NO under the action of thiol coenzyme factor, so this type of compound is a potential NO release drug; the experimental results in the rat animal model show that 3- The cyano-4-phenylfurazan oxide can be used for the chemical treatment of schistosomiasis, and the effect is better than that of the currently used drug PZQ; 4-methyl-3-(arylsulfonyl)-furazan oxide is a class of Biologically active o...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D271/08
CPCC07D271/08
Inventor 袁伟成赵建强周鸣强左键崔宝东张晓梅
Owner CHENGDU LIKAI CHIRAL TECH
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