Benzothiophene-coumarin type compound and synthesis method thereof

A technology for coumarins and benzothiophenes, which is applied in the field of benzothienocoumarins and their synthesis, can solve the problems of low reaction yield, narrow substrate range, harsh reaction conditions and the like, and achieves a high yield High, direct response, easy separation effect

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

AI Technical Summary

Problems solved by technology

However, relatively speaking, there are few reports on the specific synthesis of benzothienocoumarin 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-coumarin type compound and synthesis method thereof
  • Benzothiophene-coumarin type compound and synthesis method thereof
  • Benzothiophene-coumarin type compound and synthesis method thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0044] Preparation of 8-methyl-6H-benzo[4,5]thieno[3,2-c]chromen-6-one

[0045]4-(4-methylphenylthio)coumarin (0.20mmol), palladium acetate (5mol%), silver acetate (0.40mmol) and propionic acid (1ml) were added as solvents to a 10ml dry Schlenk tube, 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 44.63 mg of white powder with a yield of 85%. The structural formula of the resulting product is as follows:

[0046]

[0047] Such as figure 1 and figure 2 Shown, product NMR characterization: 1 HNMR (400MHz, CDCl 3 )δ8.52(s,1H),7.76(t,J=8.4Hz,2H),7.57-7.49(m,1H),7.45(d,J=8.2Hz,1H),7.33(t,J=9.1 Hz,2H),2.54(s,3H). 13 C NMR (101MHz, CDCl 3 )δ159.09, 157.64, 151.72, 140.04, 136.04, 132.58, ...

Embodiment 2

[0049] Preparation of 8-methyoxy-6H-benzo[4,5]thieno[3,2-c]chromen-6-one

[0050] Add 4-(4-methoxyphenylthio)coumarin (0.20mmol), palladium dichloride (10mol%), silver oxide (0.40mmol) and dimethylsulfoxide to a 10ml dry Schlenk tube (1.5ml) as solvent. Heat and stir at 140°C for 12 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 45.12 mg of white powder with a yield of 80%. The structural formula of the resulting product is as follows:

[0051]

[0052] Such as image 3 and Figure 4 Shown, product NMR characterization: 1 H NMR (400MHz, CDCl 3 )δ8.19(d, J=2.3Hz, 1H), 7.76(d, J=8.7Hz, 2H), 7.55(t, J=7.7Hz, 1H), 7.47(d, J=8.2Hz, 1H) ,7.35(t,J=7.5Hz,1H),7.12(dd,J=8.8,2.4Hz,1H),3.96(s,3H). 13 CNMR (1...

Embodiment 3

[0054] Preparation of 8-fluoro-6H-benzo[4,5]thieno[3,2-c]chromen-6-one

[0055] Add 4-(2-fluorophenylthio)coumarin (0.20mmol), bistriphenylphosphine palladium dichloride (15mol%), copper acetate (0.20mmol) and ethanol ( 1ml) as solvent. Heat and stir at 60°C for 24 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 43.78 mg of white powder with a yield of 81%. The structural formula of the resulting product is as follows:

[0056]

[0057] Such as Figure 5 and Figure 6 Shown, product NMR characterization: 1 H NMR (400MHz, CDCl 3 )δ8.51(d, J=8.0Hz, 1H), 7.83(dd, J=7.8, 1.4Hz, 1H), 7.62(t, J=7.1Hz, 1H), 7.56(dd, J=8.0, 5.1 Hz, 1H), 7.51(d, J=7.6Hz, 1H), 7.41(t, J=7.5Hz, 1H), 7.27–7.21(m, 1H). 13 C NM...

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Abstract

The invention discloses a benzothiophene-coumarin type compound and a synthesis method thereof. The synthesis method comprises the following steps: firstly, weighing 4-thiophenyl coumarin as raw material; 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-coumarin 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 benzothienocoumarin compound and a synthesis method thereof. Background technique [0002] It is well known that coumarin 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 benzothienocoumarin derivatives. However, relatively speaking, there are few reports on the specific synthe...

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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