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Preparation method of multi-substituted thiochromanone derivative

A technology for thiochromanone and its derivatives, which is applied in the field of preparation of multi-substituted thiochromanone derivatives, can solve the problems of harsh conditions, cumbersome synthesis steps, unfriendly environment, etc., and achieve easy purification, simple synthesis method, and synthesis The scientific and reasonable effect of the method

Inactive Publication Date: 2016-11-09
QINGDAO UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0011] Utilizing the above method to prepare thiochromanone derivatives in the laboratory has obvious disadvantages: 1) the reagent acid chlorides, acids or strong bases used are not environmentally friendly; 2) the reaction requires low temperature operation and harsh conditions; 3) the synthesis steps are cumbersome and The yield is not high

Method used

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  • Preparation method of multi-substituted thiochromanone derivative
  • Preparation method of multi-substituted thiochromanone derivative
  • Preparation method of multi-substituted thiochromanone derivative

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] 1) Preparation of Thiochromanone Derivative 3a

[0030]

[0031] Add β-carbonyldithiocarboxylate methyl ester 2a (0.5mmol, 105mg), CuI (0.5mmol, 95mg), o-phenanthroline (0.5mmol, 90.1mg) and t-BuONa (2.0mmol ,192mg). Add toluene (1.5mL), pre-stirrer at 80°C under nitrogen atmosphere for 5 minutes, slowly drop o-bromoacetophenone 1a (1.0mmol, 190mg) into the system, finish the drop within 5 minutes, and continue the reaction for 4 hours. After the reaction is complete, cool to room temperature, add dilute hydrochloric acid (1M) to adjust to weak acidity, then extract 3 times with ethyl acetate, wash the organic phase with saturated NaCl and wash with anhydrous MgSO 4 Dry for 30 minutes, remove the solvent with a rotary evaporator, and separate the residue by column chromatography (200-300 mesh silica gel) (petroleum ether / ethyl acetate=5 / 1) to obtain a yellow solid thiochromanone derivative 3a. The rate is 82%.

[0032] Spectral analysis data 3a:

[0033] 1 H NMR...

Embodiment 2

[0035] Replace 2a in Example 1 with 2b, and other conditions are the same as Example 1. The experimental results are shown in Table 1.

[0036]

[0037] Spectrum analysis data 3b:

[0038] 1 H NMR (CDCl 3 ,500MHz)δ:4.32(s,2H),6.92(s,1H),7.34-7.37(m,1H),7.44-7.46(m,2H),7.52-7.53(m,1H),7.57-7.60( m,2H),8.45(d,J=8.0Hz,1H); 13 C NMR (CDCl 3 ,125MHz)δ:50.0,126.2,127.0,127.2,127.7,128.5,129.5,130.7,131.5,132.6,137.5,137.8,146.8,180.3,196.5; HRMS(ESI-TOF):calcd for C 17 h 12 o 2 SCl[M+H] + :315.0247,found:315.0250.

Embodiment 3

[0040] Replace 2a in Example 1 with 2c, and other conditions are the same as Example 1. The experimental results are shown in Table 1.

[0041]

[0042] Spectrum analysis data 3c:

[0043] 1 H NMR (CDCl 3,500MHz)δ:4.27(s,2H),6.89(s,1H),7.21-7.25(m,2H),7.66(d,J=8.4Hz,2H),7.87(d,J=8.45Hz,2H ),8.52(dd, 1 J=8.85Hz, 2 J=5.9Hz,1H); 13 C NMR (CDCl 3 ,125MHz)δ:45.6,45.7,112.1(d, 2 J C-F =24.48Hz), 116.5(d, 2 J C-F =22.29Hz), 127.1, 127.4, 129.6, 129.9, 131.7 (d, 3 J C-F =8.98Hz), 132.4, 134.3, 139.5, 146.8, 164.1 (d, 1 J C-F =256.39Hz), 179.3, 192.5; HRMS (ESI-TOF): calcd for C 17 h 11 o 2 FSBr[M+H] + :376.9647,found:376.9649.

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Abstract

The invention discloses a preparation method of a multi-substituted thiochromanone derivative, and belongs to the technical field of organic synthesis. The method comprises the steps of: adding beta-carbonyl dithiocarbonic acid, substituted o-bromoacetophenone, copper iodide, phenanthroline and sodium tert-butoxide to a reactor, adding toluene as a solvent, and heating to the end of the reaction under the protection of nitrogen; after cooling, adding hydrochloric acid to adjust the pH into a neutral state; extracting three times with ethyl acetate, combining the organic phase, adding magnesium sulfate, drying, filtering, concentrating the filtrate in a rotary evaporator to obtain a crude product, and isolating by column chromatography silica gel to obtain the product. The method synthesis method of the multi-substituted thiochromanone derivative provided by the invention is scientific, reasonable, and simple; and the product is easy to be purified. The reaction equation is as follows.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a preparation method of polysubstituted thiochromanone derivatives. Background technique [0002] Thiochromanone, a thio-homologue of benzopyrone, is a potential drug candidate. Studies have shown that these compounds are easy to pass through the fungal cell membrane, change the ultrastructure of the fungal cell, and then destroy the structure and function of the cell membrane and cell wall, causing the cell content to flow out and lead to the death of the fungus. Therefore, many thiochromanone compounds show anti- Antibacterial, antifungal (J.Het.Chem.1985, 22, 1593) and antiviral (Bioorg.Med.Chem.2008, 16, 10319) activities. Moreover, 3-alkenyl substituted thiochromanones exhibit good antitumor and anticancer activities (J.Org.Chem. 2005, 70, 7179). Some derivatives are used as antimalarial drugs (J.Med.Chem.1978, 21, 643), and have the function of rever...

Claims

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Application Information

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IPC IPC(8): C07D335/06C07D409/06
CPCC07D335/06C07D409/06
Inventor 李明宁加彬文丽荣
Owner QINGDAO UNIV OF SCI & TECH
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