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Benzothiophene-pyrone type compound and synthesis method thereof

A technology of benzothiophene and pyrone, which is applied in the field of benzothienopyrone compounds and synthesis thereof, can solve the problems of narrow substrate range, low reaction yield, harsh reaction conditions and the like, achieves direct reaction, The effect of high yield and easy separation

Inactive Publication Date: 2019-04-26
SHAANXI UNIV OF SCI & TECH
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, relatively speaking, there are few reports on the specific synthesis of benzothienopyrone derivatives, [a) Yao, T.L.; Yue, D.; Larock, R.C.J.Org.Chem.2005,70,9985. b) Kapdi.A.R.; Karbelkar.A.; Naik.M.RSC.Adv.2013, 3, 20905. c) Lee, T H.; Jayakumar, J.; .d) Yang, Y.H.; Qi X.Y.; Liu R.L.RSC.Adv.2016,6,103895.]
These methods have the disadvantages of harsh reaction conditions, narrow substrate scope, and low reaction yields.

Method used

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  • Benzothiophene-pyrone type compound and synthesis method thereof
  • Benzothiophene-pyrone type compound and synthesis method thereof
  • Benzothiophene-pyrone type compound and synthesis method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040] Preparation of 6-methyl-3-methyl-1H-benzo[4,5]thieno[3,2-c]pyran-1-one

[0041] Add 6-methyl-4-(4-methylphenylthio)pyrone (0.20mmol), palladium acetate (10mol%), copper trifluoromethanesulfonate (0.40mmol ) and ethanol (1ml) as solvent. Heat and stir at 140°C for 2 hours, monitor the progress of the reaction with TLC, extract with saturated sodium bicarbonate (3×5ml) and ethyl acetate (3×5ml) after the reaction is complete, combine the organic phases, dry and filter over anhydrous magnesium sulfate Concentrate and separate by silica gel column chromatography to obtain 37.71 mg of white powder with a yield of 82%. The structural formula of the product obtained is as follows:

[0042]

[0043] Such as figure 1 and figure 2 Shown, product NMR characterization: 1 H NMR (400MHz, CDCl 3)δ8.32(s,1H),7.62(d,J=8.2Hz,1H),7.19(d,J=7.0Hz,1H),6.48(s,1H),2.45(s,3H),2.30( s,3H). 13 C NMR (101MHz, CDCl 3 )δ158.53, 158.47, 153.42, 136.29, 135.69, 134.39, 127.57, 124.33, 121....

Embodiment 2

[0045] Preparation of 8-bromo-3-methyl-1H-benzo[4,5]thieno[3,2-c]pyran-1-one

[0046] Add 6-methyl-4-(2-bromophenylthio)pyrone (0.20 mmol), palladium acetate (10 mol%), silver acetate (0.40 mmol) and dimethylmethylene to a 10 ml dry Schlenk tube, respectively. Sulfone (1ml) was used as solvent. Heat and stir at 140°C for 2 hours, monitor the progress of the reaction with TLC, extract with saturated sodium bicarbonate (3×5ml) and ethyl acetate (3×5ml) after the reaction is complete, combine the organic phases, dry and filter over anhydrous magnesium sulfate Concentrate and separate by silica gel column chromatography to obtain 38.21 mg of white powder with a yield of 65%. The structural formula of the resulting product is as follows:

[0047]

[0048] Such as image 3 and Figure 4 Shown, product NMR characterization: 1 H NMR (400MHz, CDCl 3 )δ8.53(d, J=8.9Hz, 1H), 7.59(d, J=7.7Hz, 1H), 7.42(t, J=7.9Hz, 1H), 6.61(s, 1H), 2.41(s, 3H).13C NMR (101MHz, CDCl 3 )δ159.53, 1...

Embodiment 3

[0050] Preparation of 6-bromo-3-methyl-1H-benzo[4,5]thieno[3,2-c]pyran-1-one

[0051] Add 6-methyl-4-(4-bromophenylthio)pyrone (0.20mmol), palladium dichloride (15mol%), silver oxide (0.20mmol) and acetic acid ( 1.5ml) as solvent. Heat and stir at 110°C for 10 hours under sealing, monitor the progress of the reaction with TLC, extract with saturated sodium bicarbonate (3×5ml) and ethyl acetate (3×5ml) after the reaction is complete, combine the organic phases, dry and filter over anhydrous magnesium sulfate Concentrate and separate by silica gel column chromatography to obtain 42.91 mg of white powder with a yield of 73%. The structural formula of the resulting product is as follows:

[0052]

[0053] Such as Figure 5 and Figure 6 Shown, product NMR characterization: 1 H NMR (400MHz, CDCl 3 )δ8.36(d,J=8.0Hz,1H),7.51(td,J=8.0,5.1Hz,1H),7.22–7.12(m,1H),6.61(s,1H),2.41(s,3H ). 13 C NMR (101MHz, CDCl 3 )δ159.60, 158.48, 156.08, 153.69, 138.56, 127.96, 127.89, 123.97, ...

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Abstract

The invention discloses a benzothiophene-pyrone type compound and a synthesis method thereof. The synthesis method comprises the following steps: firstly, weighing 4-thiophenyl pyran-2-ketone as a rawmaterial; mixing the weighed raw material with a solvent, and adding a catalyst and an oxidant to carry out a heating reaction; separating and purifying the obtained reaction product to obtain the benzothiophene-pyrone type compound. Defects that present synthesis reactions have harsh conditions, a substrate is hard to prepare, the reaction yield is low, and the like, can be avoided, reaction steps are simplified, and the reaction yield is increased.

Description

technical field [0001] The invention belongs to the field of organic synthesis, and in particular relates to a benzothienopyrone compound and a synthesis method thereof. Background technique [0002] It is well known that pyrone and thiophene derivatives are important heterocyclic compounds, which widely exist in natural products and many drug molecules. The strategies for synthesizing these two compounds have reached a relatively mature level. [a) MacDowell, D.W.; Jourdenais, R.A.; Naylor, R.W.; J. Org. Chem. 1972, 37, 4406. b) Bolognese, A.; Correale, G.; , E.; Lavecchia, A.J.Med.Chem.2008,51,8148.c) Li, C.; Liu, M.; Pschirer, N.G.; Baumgarten, M.; 6817.d) Lin, Y.; Li, Y.; Zhan, X. Chem. Soc. Rev. 2012, 41, 4245.]. Based on the practicability and importance of these two heterocyclic compounds, chemists have been continuously exploring the synthesis methods of benzothienopyrone derivatives. However, relatively speaking, there are few reports on the specific synthesis of...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D495/04
CPCC07D495/04
Inventor 张金庄瑜瑜何媛马养民
Owner SHAANXI UNIV OF SCI & TECH
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