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Method for closed-loop synthesis of benzoglioxaline and benzothiazole compounds by catalytic oxidation of primary alcohol

A technology of benzimidazole and benzothiazole, applied in the field of organic synthesis, which can solve the problems of environmental pollution, low yield, cumbersome post-processing, etc.

Inactive Publication Date: 2012-05-09
EAST CHINA UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Commonly used oxidants are mainly MnO 2 , Pb(OAc) 4 (high lead acetate), DDQ (2,3-dichloro-5,6-dicyano-1,4-benzoquinone), Oxone (potassium hydrogen persulfate preparation), etc., but because the oxidizing agent used often needs to be greatly Excessive, resulting in cumbersome post-processing, serious environmental pollution, and the yield is not too high

Method used

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  • Method for closed-loop synthesis of benzoglioxaline and benzothiazole compounds by catalytic oxidation of primary alcohol
  • Method for closed-loop synthesis of benzoglioxaline and benzothiazole compounds by catalytic oxidation of primary alcohol
  • Method for closed-loop synthesis of benzoglioxaline and benzothiazole compounds by catalytic oxidation of primary alcohol

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] Synthesis of 2-phenyl-1H-benzimidazole

[0028] The reaction was carried out in a 316L stainless steel kettle (100 mL) with a Teflon lining equipped with a magnet, and the air in the kettle was not replaced by oxygen before the reaction. First add 10mL dichloromethane into the autoclave, then add 10.0mmol benzyl alcohol and 0.1mmol TEMPO into 10mL solvent, and then add 0.15mmol iron nitrate [Fe(NO 3 ) 3 ·9H 2 O], sealed. The autoclave was filled with air pressure to 0.8 MPa, and transferred to an oil bath that had been pre-heated to 80° C. After reacting for 0.5 hours, the stirring was stopped, and the pressure was reduced to room temperature. Sampling analysis adopts Agilent 7890N gas chromatograph, HP-5 gas chromatographic column (30m×0.25mm), FID detector, the detector temperature is 300℃, the inlet temperature is 300℃, and the furnace temperature is programmed to increase: 70℃ maintain After 2 minutes, the temperature was raised to 300°C at 10°C / min and held at 300°C ...

Embodiment 2

[0032] The test method and procedure are the same as in Example 1, but the transition metal salt used is copper nitrate [Cu(NO 3 ) 2 ·2.5H 2 O], the reaction temperature is 80 ℃, the first step of reaction is 1 hour after benzyl alcohol is completely converted into benzaldehyde, then o-phenylenediamine is added to it, the reaction is 6 hours, the yield of 2-phenyl-1H-benzimidazole 92%.

Embodiment 3

[0034] The test method and procedure are the same as in Example 1, but the transition metal salt used is chromium nitrate [Cr(NO 3 ) 3 ·9H 2 O], the reaction temperature is 80 ℃, the first step of reaction is 1 hour after benzyl alcohol is completely converted into benzaldehyde, then o-phenylenediamine is added to it, the reaction is 6 hours, the yield of 2-phenyl-1H-benzimidazole 93%.

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Abstract

The invention relates to a method for closed-loop synthesis of benzoglioxaline and benzothiazole compounds by catalytic oxidation of primary alcohol. The method comprises the following steps of: with a primary alcohol compound as an initial raw material, adding a catalyst and an oxidant and oxidizing in an organic solvent to form aldehyde; and respectively carrying out one kettle way oxidation closed-loop reaction on the aldehyde and an o-phenylenediamine compound or an o-aminobenzenethiol compound at the reaction temperature of 0-150DEG C for 1-36 hours to generate corresponding benzoglioxaline and benzothiazole compounds. The method disclosed by the invention has the advantages that the method is generally suitable for benzyl alcohol, aromatic allyl alcohol and aromatic primary alcohol containing hetero atoms such as N, O, S and the like and is simple for operation; the obtained product has high quality and higher yield; a catalyst is low in price and easily-accessible; and raw materials have low cost.

Description

【Technical Field】 [0001] The invention relates to the technical field of organic synthesis, in particular to a method for catalyzing and oxidizing primary alcohols to synthesize benzimidazole and benzothiazole compounds by ring closure. 【Background technique】 [0002] Benzimidazole and benzothiazole heterocyclic compounds have a wide range of biological activities such as anti-cancer, anti-fungal, anti-parasitic, anti-rheumatism, anti-inflammatory, treatment of hypoglycemia and physiological disorders, etc., in the fields of pesticides, medicine and chemical engineering Has a wide range of applications. Therefore, the research on the synthetic methods of these two types of compounds has never stopped for decades and is still very active. [0003] A traditional synthesis method is mainly based on carboxylic acid and its carboxylic acid derivatives as starting materials, respectively, with o-phenylenediamine and o-aminothiophenol compounds through condensation and ring-closing react...

Claims

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Application Information

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IPC IPC(8): C07D277/66C07D277/64C07D405/04C07D401/04C07D409/04
Inventor 梁鑫淼王心亮柯燕雄方成斌张志光梁图
Owner EAST CHINA UNIV OF SCI & TECH
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