Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

C2 substituted 2H-benzothiazole aryl acylated derivative, and synthesis method and application thereof

A technology of benzothiazole aryl acylation and synthesis method, which is applied in the field of C2-substituted 2H-benzothiazole aryl acylation derivatives and synthesis thereof, can solve the problem of reduced yield, flammable and explosive organic peroxide oxidant, Problems such as the increase of reaction by-products

Active Publication Date: 2021-07-06
ZHEJIANG UNIV OF TECH
View PDF5 Cites 2 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although this method is milder than the above reaction, the flammable and explosive characteristics of the organic peroxide oxidant used make its use, especially the scale-up reaction, have certain limitations.
At the same time, the above reactions all use aryl methyl ketone as the carbonyl source, but because the ketone is easily oxidized or reduced, it will lead to problems such as increased reaction by-products and reduced yield.

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • C2 substituted 2H-benzothiazole aryl acylated derivative, and synthesis method and application thereof
  • C2 substituted 2H-benzothiazole aryl acylated derivative, and synthesis method and application thereof
  • C2 substituted 2H-benzothiazole aryl acylated derivative, and synthesis method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024]Example 1 Synthesis of derivative Ia ((R)n=hydrogen, (R')m=hydrogen)

[0025] Weigh 2 H - Benzothiazole (0.3 mmol, 40.6 mg), toluene (7.5 mmol, 691.1 mg), Selectfluor (0.6 mmol, 212.6 mg) and trifluoroacetic acid (0.3 mmol, 34.2 mg) in a 25 mL reaction tube, and then added 2 mL of acetonitrile, reacted at 80 °C in air atmosphere, monitored by TLC, the reaction was completed after about 10 h, the reaction solution was extracted with dichloromethane, the organic layer was concentrated to remove the solvent, and the concentrated solution was separated by column chromatography (eluent: Volume ratio 1: 0.05 petroleum ether-ethyl acetate mixed solvent) to obtain a yellow solid, ie derivative Ia. The yield is 85%.

[0026] of the compound 1 H NMR and 13 C NMR analysis data are described below,

[0027] 1 H NMR (500 MHz, CDCl 3 ) δ 8.58 (dd, J = 8.5, 1.0 Hz, 2H), 8.28 – 8.25(m, 1H), 8.07 – 8.03 (m, 1H), 7.72 – 7.67 (m, 1H), 7.63 – 7.56 (m, 4H); 13 CNMR (125 MHz, CDCl...

Embodiment 2

[0031] Example 2 Synthesis of derivative Ib ((R)n=hydrogen, (R')m=4-methyl)

[0032] Weigh 2 H - Benzothiazole (0.3 mmol, 40.6 mg), p-xylene (8.0 mmol, 848.6 mg), Selectfluor (0.3 mmol, 106.3 mg) and trifluoroacetic acid (0.45 mmol, 51.3 mg) in a 25 mL reaction tube, and then Add 2 mL of acetonitrile, react at 70 °C in an air atmosphere, and monitor by TLC. After about 8 h, the reaction is completed. The reaction solution is extracted with dichloromethane, the organic layer is concentrated to remove the solvent, and the concentrated solution is separated by column chromatography (elution The solvent is petroleum ether-ethyl acetate mixed solvent with a volume ratio of 1:0.05) to obtain a yellow solid, i.e. derivative Ib. The yield is 96%.

[0033] of the compound 1 H NMR and 13 C NMR analysis data are described below,

[0034] 1 H NMR (500 MHz, CDCl 3 ) δ 8.50 (d, J = 8.5 Hz, 2H), 8.28 – 8.24 (m,1H), 8.05 – 8.02 (m, 1H), 7.62 – 7.54 (m, 2H), 7.38 (d, J = 8.0 Hz, 2...

Embodiment 3

[0036] Example 3 Synthesis of derivative Ic ((R)n=hydrogen, (R')m=3-methyl)

[0037] Weigh 2 H - Benzothiazole (0.3 mmol, 40.6 mg), m-xylene (8.0 mmol, 848.6 mg), Selectfluor (0.3 mmol, 106.3 mg) and trifluoroacetic acid (0.45 mmol, 51.3 mg) in a 25 mL reaction tube, and then Add 2 mL of acetonitrile, react at 70 °C in an air atmosphere, and monitor by TLC. After about 8 h, the reaction is completed. The reaction solution is extracted with dichloromethane, the organic layer is concentrated to remove the solvent, and the concentrated solution is separated by column chromatography (elution The solvent is petroleum ether-ethyl acetate mixed solvent with a volume ratio of 1:0.05) to obtain a yellow solid, namely the derivative Ic. Yield 88%.

[0038] of the compound 1 H NMR and 13 C NMR analysis data are described below,

[0039] 1 H NMR (500 MHz, CDCl 3 ) δ 8.40 (d, J = 7.5 Hz, 1H), 8.30 (s, 1H), 8.29– 8.26 (m, 1H), 8.05 – 8.03 (m, 1H), 7.63 – 7.57 (m, 2H), 7.51 – 7.45 ...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

Abstract

The invention discloses a C2 substituted 2H-benzothiazole aryl acylated derivative, and a synthesis method and application thereof. The preparation method of the derivative comprises the following steps: mixing substituted 2H-benzothiazole and substituted methyl benzene, adding into a solvent, in the presence of an oxidizing agent Selectfluor and an additive trifluoroacetic acid, carrying out a heating and stirring reaction in the air atmosphere, performing TLC monitoring is conducted till the reaction is finished, and separating and purifying the obtained reaction liquid to obtain the target product C2 substituted 2H-benzothiazole aryl acylated derivative. The substituted methyl benzene used in the invention is low in price, easy to obtain and good in chemical stability, the method has the advantages of being high in atom economy, simple in catalytic system, free of transition metal catalysts, good in product yield, wide in substrate range and the like, and the prepared compound structure can be further optimized as an anti-tumor drug lead.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, in particular to a C2-substituted 2 H - Benzothiazole aryl acylated derivatives and their synthesis methods and applications. Background technique [0002] 2 replaced by C2 H - Benzothiazole derivatives have a high degree of structural diversity and a wide range of biological activities, and are widely found in natural products and synthetic compounds. They have broad application prospects in the fields of medicine, pesticides, and industry. In the field of pesticides, it has insecticidal (Chin. J. Org., Chem. 2012, 32, 957), bactericidal (J. Am. Chem.Soc., 2008, 130, 2900), antiviral (Chin. J. Org. , Chem. 2014, 34, 419) and other biological activities; in the field of medicine, it has antibacterial (Mini-Rev. Org. Chem., 2012, 9, 44), antitumor (Curr. Med.Chem., 2009, 16, 2430 ), anticancer (J. Clin. Endocr. Metab., 1998, 83, 4474) and other biological activities; in industry, it c...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
IPC IPC(8): C07D277/64A61P35/00
CPCC07D277/64A61P35/00
Inventor 翁建全孙晓彤孔瑶蕾刘幸海
Owner ZHEJIANG UNIV OF TECH
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com