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Method for preparing 1, 3-benzothiazole derivative through efficient catalysis of potassium tert-butoxide

A technology of potassium tert-butoxide and benzothiazole, which is applied in the field of efficient preparation of 1,3-benzothiazole derivatives, can solve the problems of complex substrate structure, long reaction time, cumbersome post-processing, etc. Stable, low-dose effect

Active Publication Date: 2020-01-17
SHAANXI NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] The common 1,3-benzothiazole synthesis methods generally have defects such as complex substrate structure / use of noble metals, long reaction time, high temperature, and cumbersome post-treatment. Therefore, researchers have never stopped looking for milder, Efficient and Green Catalytic Synthesis of 1,3-Benzothiazole

Method used

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  • Method for preparing 1, 3-benzothiazole derivative through efficient catalysis of potassium tert-butoxide
  • Method for preparing 1, 3-benzothiazole derivative through efficient catalysis of potassium tert-butoxide
  • Method for preparing 1, 3-benzothiazole derivative through efficient catalysis of potassium tert-butoxide

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0015] Preparation of 2-phenyl-1,3-benzothiazole with the following structural formula

[0016]

[0017] Add 0.103g (0.5mmol) 1,4-diphenyl-3-butyne-2-one, 0.0028g (0.025mmol) potassium tert-butoxide, 112μL (1.05mmol) anthranilin to the reaction flask, 1mL of tert-butanol, stirred and reacted at 50°C for 5 hours, stopped the reaction, added 5mL of distilled water, added 10mL of ethyl acetate to extract 3 times, rotatively evaporated the organic phase to remove ethyl acetate, and separated it with a silica gel column (the eluent was petroleum The volume ratio of ether and dichloromethane is 2:1 mixed solution), obtains 2-phenyl-1,3-benzothiazole, and its productive rate is 99%, and the spectral data of product is: 1 H NMR (400MHz, CDCl 3 )δ8.17-8.09(m,3H),7.95-7.88(m,1H),7.56-7.48(m,4H),7.44-7.36(m,1H); 13 C NMR (101MHz, CDCl 3 )δ168.98, 155.03, 135.97, 134.51, 131.90, 129.94, 128.49, 127.25, 126.12, 124.16, 122.55.

Embodiment 2

[0023] Preparation of 2-(4-tolyl)-1,3-benzothiazole with the following structural formula

[0024]

[0025] In this example, the 1,4-diphenyl-3-butane used in Example 1 was replaced with equimolar 1-phenyl-4-(4-methylphenyl)-3-butyn-2-one Alkyn-2-one, other steps are the same as in Example 1, to obtain 2-(4-tolyl)-1,3-benzothiazole, the yield is 99%, and the spectral data of the product is: 1 H NMR (400MHz, CDCl 3 )δ7.95(d, J=8.1Hz, 1H), 7.90-7.84(m, 2H), 7.76(d, J=8.0Hz, 1H), 7.39-7.33(m, 1H), 7.28-7.21(m ,1H),7.17(d,J=7.9Hz,2H),2.30(s,3H); 13 C NMR (101MHz, CDCl 3 )δ168.21, 154.21, 141.39, 134.98, 131.00, 129.71, 127.50, 126.23, 124.99, 123.07, 121.56, 21.52.

Embodiment 3

[0027] Preparation of 2-thienyl-1,3-benzothiazole with the following structural formula

[0028]

[0029] In this example, the 1,4-diphenyl-3-butyn-2-one used in Example 1 was replaced with equimolar 1-phenyl-4-thienyl-3-butyn-2-one, Other steps are the same as in Example 1 to obtain 2-thienyl-1,3-benzothiazole with a yield of 84%, and the spectral data of the product are: 1 H NMR (400MHz, CDCl 3 )δ8.06(d, J=8.2Hz, 1H), 7.84(d, J=8.0Hz, 1H), 7.65(d, J=3.5Hz, 1H), 7.52-7.46(m, 2H), 7.40- 7.34(m,1H),7.13(dd,J=5.1,3.8Hz,1H); 13 C NMR (101MHz, CDCl 3 )δ162.27, 154.62, 138.26, 135.63, 130.19, 129.52, 128.95, 127.33, 126.13, 123.88, 122.36.

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Abstract

The invention discloses a method for preparing 1, 3-benzothiazole derivative through efficient catalysis of potassium tert-butoxide. According to the method, a 1-phenyl-3-butyne-2-ketone compound andan o-aminothiophenol compound are taken as raw materials, potassium tert-butoxide is taken as a catalyst and tert-butyl alcohol is taken as a solvent to prepare the 1, 3-benzothiazole derivative at high efficiency and high yield. According to the method, no metal catalyst is used, the method is environmentally friendly, reaction conditions are mild, operation is easy, the 1, 3-benzothiazole derivative can be obtained only by conducting simple column chromatography separation on a product obtained after the reaction is finished, a new green and efficient way is developed for preparation of the1, 3-benzothiazole derivative, and certain application prospects are achieved.

Description

technical field [0001] The invention relates to a method for efficiently preparing 1,3-benzothiazole derivatives by catalyzing the reaction of 1-phenyl-3-butyn-2-one compounds and o-aminobenzenethiol compounds with potassium tert-butoxide. Background technique [0002] 1,3-Benzothiazole derivatives, as a special substance containing sulfur and nitrogen heterocyclic structure, have important applications in medicinal chemistry. Due to their unique pharmacological properties and biological activities, many 1,3-benzothiazole derivatives Drugs with thiazole as the core structure have been used clinically and commercialized. Benzothiazole derivatives have been widely used in the treatment of various diseases over the years, such as Alzheimer's disease, anti-inflammation, diabetes, tuberculosis, anti-cancer, antibacterial, etc. At the same time, it can also be used as an orexin receptor anti-caking agent , calcium anti-binding activity, and various enzyme inhibitors are widely us...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D277/66C07D417/10
CPCC07D277/66C07D417/10Y02P20/584
Inventor 高子伟周玉杰杨明明孙华明吴亚
Owner SHAANXI NORMAL UNIV
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