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3-thiobenzofuran derivative and synthesis method thereof

A technology of benzofuran and synthesis method, applied in the field of 3-thiobenzofuran derivatives and synthesis thereof, achieves the effects of simple preparation method and operation, good functional group diversity, and improved molar yield

Pending Publication Date: 2021-11-02
QILU UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the 2-position substitution in the structure of the obtained product is limited to alkyl or aryl, and there is no explanation for heterocycles commonly used in drug synthesis, especially nitrogen-containing heterocycles

Method used

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  • 3-thiobenzofuran derivative and synthesis method thereof
  • 3-thiobenzofuran derivative and synthesis method thereof
  • 3-thiobenzofuran derivative and synthesis method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] A kind of synthetic method of 3-thiobenzofuran derivatives, comprising steps:

[0039]

[0040] For the synthesis method of 3-hydroxy-3-((2-hydroxyphenyl)ethynyl)-1-methylindol-2-one (IIa), please refer to the literature "Org. Biomol. Chem., 2018, 16, 6133" .

[0041]The preparation steps of compound Ia are: add compound IIa (27.9mg, 0.1mmol) in 10mL round bottom flask, methylene chloride 2ml, thiophenol IIIa (13.2mg, 0.12mmol), add boron trifluoride diethyl ether ( 17mg, 0.12mmol), reacted at 25°C for 12 hours under the protection of nitrogen. Separation by silica gel column chromatography (eluent: petroleum ether (60-90° C.) / ethyl acetate=8:1, V:V) gave light yellow solid Ia (32.3 mg, molar yield 87%) with a purity greater than 95%. The target product was confirmed by NMR and high-resolution mass spectrometry.

[0042] Characterization data of compound Ia: light yellow solid, melting point 197-198°C;

[0043] NMR spectrum such as figure 1 As shown, the NMR da...

Embodiment 2

[0046] A kind of synthetic method of 3-thiobenzofuran derivatives, comprising steps:

[0047]

[0048] For the synthesis method of compound IIb, please refer to the literature "Org. Biomol. Chem., 2018, 16, 6133".

[0049] The preparation steps of compound Ib are: add compound IIb (35.7mg, 0.1mmol) in 10mL round bottom flask, methylene chloride 2ml, thiophenol IIIa (13.2mg, 0.12mmol), add boron trifluoride diethyl ether ( 17mg, 0.12mmol), reacted at 25°C for 12 hours under the protection of nitrogen. Separation by silica gel column chromatography (eluent: petroleum ether (60-90° C.) / ethyl acetate=8:1, V:V) gave light yellow solid Ib (38.2 mg, molar yield 85%) with a purity greater than 95%. The target product was confirmed by NMR and high-resolution mass spectrometry.

[0050] Characterization data of compound Ib: light yellow solid, melting point 220-221°C;

[0051] The NMR data are as follows:

[0052] 1 H NMR (400MHz, CDCl3) δ7.47(d, J=7.7Hz, 1H), 7.44–7.36(m, 2H),...

Embodiment 3

[0054] A kind of synthetic method of 3-thiobenzofuran derivatives, comprising steps:

[0055]

[0056] For the synthesis method of compound IIc, please refer to the literature "Org. Biomol. Chem., 2018, 16, 6133"

[0057] The preparation steps of compound Ic are: add compound IIc (35.5mg, 0.1mmol) in 10mL round bottom flask, dichloromethane 2ml, thiophenol IIIa (13.2mg, 0.12mmol), add boron trifluoride diethyl ether ( 17mg, 0.12mmol), reacted at 25°C for 12 hours under the protection of nitrogen. Separation by silica gel column chromatography (eluent: petroleum ether (60-90° C.) / ethyl acetate=8:1, V:V) gave light yellow solid Ib (40.2 mg, molar yield 90%) with a purity greater than 95%. The target product was confirmed by NMR and high-resolution mass spectrometry.

[0058] Characterization data of compound Ic: pale yellow solid, melting point 242-243°C;

[0059] 1 H NMR (400MHz, CDCl 3 )δ7.45(d,J=7.3Hz,1H),7.42–7.35(m,3H),7.30(dt,J=13.6,5.6Hz,6H),7.26–7.18(m,4H),7.18–...

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Abstract

The invention provides a 3-thiobenzofuran derivative and a synthesis method thereof. The preparation method comprises the steps of carrying out Meyer-Schuster rearrangement / nucleophilic addition / intramolecular cyclization reaction on an isatin-derived propargyl alcohol compound and thiophenol in an organic solvent under the action of an acidic reagent to obtain the 3-thiobenzofuran derivative. The raw materials are cheap and easy to obtain, the steps are simple, the reaction conditions are easy to realize, the 3-sulfo and 2-substituted benzofuran derivative can be prepared by a one-pot method, the yield of the target product is high, and the product has very good functional group diversity and is beneficial to subsequent application.

Description

technical field [0001] The invention relates to a 3-thiobenzofuran derivative and a synthesis method thereof, belonging to the field of new drug research and development. Background technique [0002] The benzofuran structure is a kind of compound skeleton widely existing in natural products and drug molecules. Natural products containing a benzofuran skeleton exhibit good biological activities, such as anti-tumor, anti-fungal, anti-oxidant, anti-inflammatory, etc., so the synthesis of such compounds is of great significance (see A.H.Banskota, Y.Tezuka, K.Midorikawa , K. Matsushige, S. Kadota, J. Nat. Prod. 2000, 63, 1277-1279). Among them, 3-thiobenzofuran has changed the electronegativity and physical and chemical properties of the molecule as a whole due to the doping of sulfur heteroatoms (see X.Zhao, L.Zhang, X.Lu, T.Li, K.Lu, J.Org.Chem.2015,80,2918–2924), has a wider application prospect. [0003] The existing synthesis of 3-thiobenzofuran is mainly realized by ele...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D405/04
CPCC07D405/04
Inventor 孙洲史娟肖加奇
Owner QILU UNIV OF TECH
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