Method for preparing dibenzothiophene derivatives

A technology for dibenzothiophene and derivatives is applied in the field of preparation of dibenzothiophene derivatives and achieves the effects of low reaction cost, simple process and mild conditions

Inactive Publication Date: 2013-03-20
ZHEJIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Lewis-acid-promoted direct preparation of dibenzothiophene from methylthio-containing triazenes has not been reported

Method used

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  • Method for preparing dibenzothiophene derivatives
  • Method for preparing dibenzothiophene derivatives
  • Method for preparing dibenzothiophene derivatives

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] In a 100 mL reaction flask, add 369 mg of methylthio-containing triazene 1a and 40 mL of acetonitrile, and then slowly add 0.256 mL of boron trifluoride diethyl ether dropwise with a 1 mL syringe. The reaction solution was stirred at 45°C for 4 hours. After the reaction, cool to room temperature, filter with a glass funnel, and purify the filtrate through a silica gel column (the volume ratio of petroleum ether and ethyl acetate is 10:1) to obtain 215 mg of the product with a yield of 80%. The reaction process is shown in the following formula :

[0029]

[0030] The product prepared in the present embodiment is carried out nuclear magnetic resonance analysis, and the results are as follows:

[0031] 1 H NMR (400 MHz, CDCl 3 ): δ 8.84(s, 1H), 8.22-8.26(m, 1H), 8.11-8.14(m, 1H), 7.84-7.90(m, 2H), 7.48-7.51(m, 2H), 4.46(q , J=6.8Hz, 2H), 1.47(t, J=7.2Hz, 3H);

[0032] 13 C NMR (100 MHz, CDCl 3 ): δ 166.7, 144.2, 139.6, 135.5, 135.2, 127.3, 126.8, 124.8, 123.1, 1...

Embodiment 2

[0034] In a 100 mL reaction flask, add 369 mg of methylthio-containing triazene 1a and 40 mL of methanol, and then slowly add 0.256 mL of boron trifluoride diethyl ether dropwise with a 1 mL syringe. The reaction solution was stirred at 45°C for 4 hours. After the reaction, cool to room temperature, filter with a glass funnel, and purify the filtrate through a silica gel column (the volume ratio of petroleum ether and ethyl acetate is 10:1) to obtain 166 mg of the product with a yield of 65%. The reaction process is shown in the following formula :

[0035]

[0036] The product prepared in the present embodiment is carried out nuclear magnetic resonance analysis, and the results are as follows:

[0037] 1 H NMR (400 MHz, CDCl 3 ): δ 8.84(s, 1H), 8.22-8.26(m, 1H), 8.11-8.14(m, 1H), 7.84-7.90(m, 2H), 7.48-7.51(m, 2H), 4.46(q, J=6.8Hz, 2H), 1.47(t, J=7.2Hz, 3H);

[0038] 13 C NMR (100 MHz, CDCl 3 ): δ 166.7, 144.2, 139.6, 135.5, 135.2, 127.3, 126.8, 124.8, 123.1, 122.8,...

Embodiment 3

[0040] In a 100 mL reaction flask, add 369 mg of methylthio-containing triazene 1a and 40 mL of toluene, and then slowly add 0.256 mL of boron trifluoride diethyl ether dropwise with a 1 mL syringe. The reaction solution was stirred at 45°C for 4 hours. After the reaction, cool to room temperature, filter with a glass funnel, and purify the filtrate through a silica gel column (the volume ratio of petroleum ether and ethyl acetate is 10:1) to obtain 103 mg of the product with a yield of 40%. The reaction process is shown in the following formula :

[0041]

[0042] The product that present embodiment prepares is carried out nuclear magnetic resonance analysis, and the result is as follows:

[0043] 1 H NMR (400 MHz, CDCl3 ): δ 8.84(s, 1H), 8.22-8.26(m, 1H), 8.11-8.14(m, 1H), 7.84-7.90(m, 2H), 7.48-7.51(m, 2H), 4.46(q, J=6.8Hz, 2H), 1.47(t, J=7.2Hz, 3H);

[0044] 13 C NMR (100 MHz, CDCl 3 ): δ 166.7, 144.2, 139.6, 135.5, 135.2, 127.3, 126.8, 124.8, 123.1, 122.8, 122.5,...

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Abstract

The invention discloses a method for preparing dibenzothiophene derivatives. The method comprises the following steps of: synthesizing dibenzothiophene derivatives with chemical formulas of (I), (III) or (IV) from methylmercapto-containing triazene compounds in an organic solvent under catalysis of lewis acid, wherein R1 is ethoxycarbonyl, cyano, hydrogen or acetyl; R2 is chlorine or methyl; R3 is chlorine; R4 is halogen, methyl or methoxyl; and R5 is styryl. The preparation method is simple and mild in reaction conditions and has wide application prospects in the industries of fine chemical engineering and pharmacy.

Description

technical field [0001] The invention relates to the field of organic synthesis, in particular to a preparation method of dibenzothiophene derivatives. Background technique [0002] Dibenzothiophene derivatives are an important class of organic compounds, dibenzothiophene and alkyl derivatives (DBTs) especially 4-methyldibenzothiophene (4-MDBT), 4,6-dimethyl Dibenzothiophene (DMBT) is considered to be the most difficult desulfurization sulfide in diesel fractions, so using DBT, 4-MDBT and 4,6-DMDBT as model compounds to study the deep desulfurization of oil products has become a hot research topic at home and abroad ( Ca talysis today, 1997, 36, 393). In addition, dibenzothiophene is also widely used in liquid crystal optoelectronic semiconductor materials. For example, the literature (J. Meter. Chem. 2007, 17, 1421) reported the research of dibenzothiophene derivatives as a new semiconductor in organic field effect transistors. [0003] One of the most important methods o...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D333/76
CPCC07D295/30C07D333/76
Inventor 陈万芝尚晓博
Owner ZHEJIANG UNIV
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