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Palladium catalyzed synthesis method of 2-(2 '-hydroxy phenyl) benzoxazole

A technology of hydroxyphenyl and benzoxazole, which is applied in the field of synthesis of 2-benzoxazole, can solve the problems of low catalytic reaction efficiency, many by-products, large usage, etc., and achieves easy implementation, few by-products, The effect of mild reaction conditions

Inactive Publication Date: 2016-04-27
INST OF AGRO FOOD SCI & TECH CHINESE ACADEMY OF AGRI SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, they generally have the disadvantages of large usage, low catalytic reaction efficiency, more by-products and certain pollution.

Method used

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  • Palladium catalyzed synthesis method of 2-(2 '-hydroxy phenyl) benzoxazole
  • Palladium catalyzed synthesis method of 2-(2 '-hydroxy phenyl) benzoxazole
  • Palladium catalyzed synthesis method of 2-(2 '-hydroxy phenyl) benzoxazole

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] This example uses Pd(OAc) 2 and Cs 2 CO 3 , DMF and a warming environment to synthesize HBO.

[0032] figure 1 The preparation route for this example is shown.

[0033] Step A, condensation reaction

[0034] Salicylaldehyde (5mg, 0.04mmol) and 2-aminophenol (9mg, 0.08mmol) were added to 15mL of anhydrous EtOH, and refluxed for 5 hours; after cooling, the solution was filtered, and the precipitate was recrystallized with anhydrous EtOH to obtain Red needle crystal Schiff base intermediate 1.

[0035] The structural formula of the intermediate 1 is:

[0036] Step B, oxidation ring formation reaction

[0037] Intermediate 1 (43mg, 0.2mmol), Pd(OAc) 2 (2.3mg, 0.01mmol) and Cs 2 CO 3 (130mg, 0.4mmol) was dissolved in 10mL of DMF (dimethylformamide) solution, stirred at room temperature for 5 minutes, then heated to 80°C, and at the same time, oxygen was continuously introduced below the liquid surface;

[0038] Step C, using TLC method (thin layer chromatography...

Embodiment 2

[0044] This example uses Pd(OAc) 2 and Cs 2 CO 3 , DMF and a warming environment to synthesize HBO.

[0045] figure 1 The preparation route for this example is shown.

[0046] Step A, condensation reaction

[0047] This step is the same as the best embodiment 1.

[0048] Salicylaldehyde (5mg, 0.04mmol) and 2-aminophenol (9mg, 0.08mmol) were added to 15mL of anhydrous EtOH, and refluxed for 5 hours; after cooling, the solution was filtered, and the precipitate was recrystallized with anhydrous EtOH to obtain Red needle crystal Schiff base intermediate 1.

[0049] The structural formula of the intermediate 1 is:

[0050] Step B, oxidation ring formation reaction

[0051] Intermediate 1 (43mg, 0.2mmol), Pd(OAc) 2 (2.3mg, 0.01mmol) and Cs 2 CO 3 (130mg, 0.4mmol) was dissolved in 10mL of DMF (dimethylformamide) solution, stirred at room temperature for 5 minutes, then heated to 60°C for reaction, and at the same time, oxygen was continuously introduced below the liquid...

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Abstract

The present invention discloses a palladium-catalyzed synthesis method of 2-(2 '-hydroxy phenyl) benzoxazole, HBO is shorted for 2-(2 '-hydroxy phenyl) benzoxazole in English, a chemical molecular formula is C14H13NO2 , the molecular structural formula is as shown in the specification, the synthesis method is as follows: firstly a condensation reaction is performed to obtain a red needle-like crystal Schiff base intermediate 1; then the intermediate 1 is oxidized for ring formation reaction to obtain the final compound HBO. The method has the following beneficial effects: the synthesis method is simple in process, readily available in raw materials, easy to implement, mild in reaction conditions, high in product yield and less in by-products, and has a wide range of application.

Description

technical field [0001] The invention belongs to the technical field of chemical synthesis, and more specifically, relates to a palladium-catalyzed 2-(2'-hydroxyphenyl) benzoxazole synthesis method. Background technique [0002] Benzoxazole compounds are benzoheterocyclic compounds containing nitrogen and oxygen atoms in their molecular structure. This type of compound has good biological activities such as antibacterial, antiseptic, herbicide, and anticancer, and has a wide range of applications in the fields of medicine, pesticide, catalysis, laser dyes, and sensors. Among them, the 2-(2'-hydroxyphenyl) benzoxazole compound has the characteristics of excited state intramolecular proton transfer (ESIPT), showing dual fluorescence emission of ketone and enol, and has a higher fluorescence quantum The advantages of productivity and larger Stokes shift (Stokesshift) have become the focus of research in many fields. Therefore, the synthetic method of 2-(2'-hydroxyphenyl) benzo...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D263/57
CPCC07D263/57
Inventor 范蓓陈卫华尚玉婷贺永桓李敏敏黄亚涛朱玉龙贺妍
Owner INST OF AGRO FOOD SCI & TECH CHINESE ACADEMY OF AGRI SCI
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