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4-alkylthio polysubstituted thiophene derivative and synthesis thereof

A technology of thiophene derivatives and dialkylthiomethylene, which is applied in the field of 4-alkylthio multi-substituted thiophene derivatives, can solve problems such as violations, and achieve the effects of simple operation, low cost, and easy industrial production

Active Publication Date: 2020-04-17
DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, these methods basically require the use of mercaptans or thioethers with strong odor and toxicity as sulfur sources, which to a certain extent violates the original intention of green chemistry and atomic economy, and many raw materials need to be vulcanized by sulfurizing reagents in advance to obtain sulfur. Carbonyl compounds, and then undergo intramolecular or intermolecular cyclization reactions to obtain thiophene derivatives

Method used

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  • 4-alkylthio polysubstituted thiophene derivative and synthesis thereof
  • 4-alkylthio polysubstituted thiophene derivative and synthesis thereof
  • 4-alkylthio polysubstituted thiophene derivative and synthesis thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0033]

[0034] In a 25 mL schlenk tube, add 3,3-dialkylthiomethylene-1,3-dicarbonyl compound 2a (0.5 mmol), ethyl diazoacetate 3a (1.0 mmol), ethylene iodide in sequence under argon Copper (10mol%) and 2.0 mL of 1,4-dioxane were stirred at 25°C for 24 hours. After cooling to room temperature, the volatile components were removed under reduced pressure, and then separated by silica gel column chromatography (eluent was petroleum ether (60-90°C) / ethyl acetate, v / v=70:1) to obtain the target product 1a (101 mg, yield 78%). The target product was confirmed by NMR and high-resolution mass spectrometry.

Embodiment 2

[0036]

[0037] In a 25 mL schlenk tube, add 3,3-dialkylthiomethylene-1,3-dicarbonyl compound 2b (0.5 mmol), ethyl diazoacetate 3a (1.0 mmol), ethylene iodide in sequence under argon Copper (10mol%) and 2.0 mL of 1,4-dioxane were stirred at 25°C for 24 hours. After cooling to room temperature, the volatile components were removed under reduced pressure, and then separated by silica gel column chromatography (eluent was petroleum ether (60-90°C) / ethyl acetate, v / v=70:1) to obtain the target product 1b (143 mg, yield 75%). The target product was confirmed by NMR and high-resolution mass spectrometry.

Embodiment 3

[0039]

[0040]The reaction steps and operations are the same as in Example 1, except that the diazonium compound is 3b. The reaction was stopped, and the target product 1c (91 mg, yield 74%) was obtained after post-processing.

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PUM

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Abstract

The invention discloses a method for synthesizing a 4-alkylthio polysubstituted thiophene derivative with potential biological activity. According to the invention, the 4-alkylthio polysubstituted thiophene derivative is generated in one step through intermolecular in-situ generation of sulfur ylide and intramolecular cyclization reaction by using a 3,3-dialkylthiomethylene-1,3-dicarbonyl compoundwith characteristics of easy preparation, structural diversity and multiple reaction centers and a diazo compound as raw materials, has a certain potential pharmaceutical activity, and can be furtherconverted into a functional product. The method has the advantages of easily available raw materials, simple operation, mild synthesis reaction conditions, high reaction efficiency, and diversity offunctional groups.

Description

technical field [0001] The invention discloses a method for synthesizing 4-alkylthio polysubstituted thiophene derivatives with potential biological activity. Using 3,3-dialkylthiomethylene-1,3-dicarbonyl compounds and diazo compounds as starting materials, CuI as a catalyst, under heating conditions, through the intermolecular [4+1] cyclization reaction, One-step generation of 4-alkylthio polysubstituted thiophene derivatives. [0002] Compared with the reported synthesis method of multi-substituted thiophene derivatives, the present invention has easy-to-obtain raw materials, simple operation, mild synthesis reaction conditions, high efficiency, yield of 50%-85%, and the product has good stereoselectivity and Functional group diversity. The carbonyl group at position 3 and the alkylthio group at position 4 in the 4-alkylthio multi-substituted thiophene skeleton structure synthesized by the invention are groups that can be further functionalized, and can be used as intermed...

Claims

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Application Information

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IPC IPC(8): C07D333/38C07D495/04
CPCC07D333/38C07D495/04
Inventor 娄江余正坤
Owner DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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