Preparation method of selenium-containing thiazoline compound

A technology for selenium thiazolines and compounds, which is applied in the field of preparation of selenium-containing thiazoline compounds, can solve the problems of cumbersome operations and the use of toxic solvents, and achieve the effects of simple operations, readily available raw materials, and scientific and reasonable synthesis methods

Inactive Publication Date: 2020-06-05
QINGDAO UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0007] The above methods have obvious shortcomings or deficiencies: high temperature heating is required, toxic solvents are used, and the operation is cumbersome, etc.

Method used

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  • Preparation method of selenium-containing thiazoline compound
  • Preparation method of selenium-containing thiazoline compound
  • Preparation method of selenium-containing thiazoline compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] Preparation of selenium-containing thiazoline compound 3a

[0021]

[0022] In the two-necked flask of 10mL, add N-allyl benzylsulfamide 1a (0.20mmol, 36mg), diphenyl diselenide 2a (0.12mmol, 38mg), LiClO 4 (0.3mmol, 32mg) and acetonitrile (4mL). Graphite felt electrodes were used as cathode and anode respectively, and electrolyzed at a constant current of 2 mA for 4 hours at room temperature. After the reaction was completed, the solvent was evaporated with a rotary evaporator, and the product was purified by silica gel flash column chromatography (petroleum ether: ethyl acetate) to obtain product 3a with a yield of 67%.

[0023] Spectral analysis data 3a:

[0024] 1 H NMR (DMSO-d 6 ,500MHz): δ7.74(d,J=7.6Hz,2H),7.48(dt,J=28.3,7.3Hz,5H),7.33–7.22(m,3H),4.42(dd,J=16.3,3.3 Hz, 1H), 4.30(dd, J=16.3, 8.1Hz, 1H), 4.22–4.14(m, 1H), 3.18(d, J=7.3Hz, 2H). 13 C NMR (DMSO-d 6 ,125MHz):δ165.5,133.3,132.4,131.8,129.8,129.8,129.2,128.4,127.5,69.7,51.3,33.2.HRMS(ESI-TOF,[M...

Embodiment 2

[0026] Replace 1a in Example 1 with 1b, and other conditions are the same as Example 1. The experimental results are shown in Table 1.

[0027]

[0028] Spectrum analysis data 3b:

[0029] 1 H NMR (DMSO-d 6 ,500MHz): δ7.64–7.60(m,2H),7.54–7.48(m,2H),7.32–7.23(m,5H),4.39(dd,J=16.3,3.6Hz,1H),4.28(dd , J=16.3, 8.0Hz, 1H), 4.20–4.13(m, 1H), 3.17(d, J=7.3Hz, 2H), 2.33(s, 3H). 13 C NMR (DMSO-d 6 ,125MHz):δ165.3,141.8,132.4,130.6,129.8,129.8,128.4,127.5,69.6,51.2,33.2,21.5.HRMS(ESI-TOF,[M+H + ]): calcd for C 17 h 18 NSSe, 348.0325, found 348.0330.

Embodiment 3

[0031] Replace 1a in Example 1 with 1c, and other conditions are the same as Example 1. The experimental results are shown in Table 1.

[0032]

[0033] Spectrum analysis data 3c:

[0034] 1 H NMR (DMSO-d 6 ,500MHz): δ7.68(d,J=8.6Hz,2H),7.51(d,J=6.9Hz,2H),7.33–7.23(m,3H),6.99(d,J=8.6Hz,2H) ,4.37(dd,J=16.1,3.5Hz,1H),4.25(dd,J=16.1,8.0Hz,1H),4.19–4.11(m,1H),3.78(s,3H),3.17(d,J =7.3Hz,2H). 13 C NMR (DMSO-d 6 ,125MHz):δ164.7,162.1,132.4,130.1,129.8,127.5,125.9,114.5,69.6,55.9,51.3,33.2.HRMS(ESI-TOF,[M+H + ]): calcd for C 17 h 18 NOSSe, 364.0274, found 364.0273.

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Abstract

The invention discloses a preparation method of a selenium-containing thiazoline compound, and belongs to the technical field of organic synthesis. The method comprises the following steps: adding thioamide, a diselenide compound, a solvent and an electrolyte into a reactor, carrying out a reaction process under the action of electrification, and carrying out silica gel column chromatography separation after the reaction is finished to obtain a pure target product. The preparation method of the selenium-containing thiazoline compound provided by the invention has the characteristics of simpleoperation, mild conditions, short reaction time and the like. The reaction equation is shown in the specification.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a preparation method of selenium-containing thiazoline compounds. Background technique [0002] Thiazolines and their derivatives are an important class of compounds that widely exist in natural products and have diverse biological activities, such as anticancer (J.Am.Chem.Soc.1990, 112, 8195), anti-HIV (Drugs2010, 70,1885) etc. At the same time, organoselenides are a class of important molecules with high pharmacological value, which widely exist in biologically active molecules. For example, anti-tumor activity (J.Med.Chem.2017, 60, 7300), inhibition of herpes virus (J.Med.Chem.2015, 58, 8734), etc. Therefore, it is of great significance to develop green and efficient new methods for the synthesis of selenium-containing thiazoline compounds. [0003] The preparation method of thiazoline compound has: [0004] 1) Pan's research group prepared thiazoline...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C25B3/00
CPCC25B3/00
Inventor 郭维斯潘超文丽荣李明
Owner QINGDAO UNIV OF SCI & TECH
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