Preparation method of sulfur-containing 3-arylmethylene isoindolinone derivative

A technology for arylmethylene isoindolinone and derivatives, which is applied in the field of preparing sulfur-containing 3-arylmethylene isoindolinone derivatives, can solve problems such as catalyst poisoning, and achieves reduction of emissions and easy product availability. Obtain and protect the health of operators

Active Publication Date: 2017-12-19
WENZHOU UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

It is well known that the methylthio group is rarely used as a directing group to build structurally different molecules, probably due to the poisoning of the catalyst by the thiol group

Method used

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  • Preparation method of sulfur-containing 3-arylmethylene isoindolinone derivative
  • Preparation method of sulfur-containing 3-arylmethylene isoindolinone derivative
  • Preparation method of sulfur-containing 3-arylmethylene isoindolinone derivative

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preparation example Construction

[0020] The present invention provides a kind of preparation method of sulfur-containing 3-aryl methylene isoindolinone derivatives, comprising the following steps: N -(2-Methylthio-phenyl)aryl formamide and aryl terminal alkynes as substrates; by adding 10 mol% Ni(dppp)Cl 2 Metal catalyst, 200 mol% Na 2 CO 3 Alkaline, O 2 Oxidant, DMSO is the reaction solvent, at a temperature of 100 o C~140 o Under the condition of C, react for 12~24 h; the chemical reaction formula is as follows:

[0021]

[0022] The Ar is phenyl, 4-methylphenyl, 4-methoxyphenyl, 4-fluorophenyl, 4-chlorophenyl, 3-chlorophenyl, 4-bromophenyl, 4-nitro One of phenyl, 4-biphenyl, 2-thienyl; Ar' is 4-methylphenyl, 4-methoxyphenyl, 4-fluorophenyl, 4-chlorophenyl, 4- One of bromophenyl, 4-nitrophenyl, 4-trifluoromethylphenyl;

[0023] After the reaction was completed, it was cooled, diluted with ethyl acetate, transferred to a separatory funnel and washed three times with saturated brine, the aqueous l...

specific Embodiment 1

[0024] Specific embodiment one: 48.7 milligrams (0.2 mmol) N -(2-Methylthio-phenyl)benzamide, 61.3 mg (0.6 mmol) phenylacetylene, 10.8 mg (0.02 mmol) Ni(dppp)Cl 2 , 42.4 mg (0.4 mmol) of anhydrous sodium carbonate was added to 2 mL of dimethyl sulfoxide solvent. Three pumps and three links in an oxygen atmosphere, after plugging in an oxygen balloon, at 140 o C oil bath was reacted for 24 hours. After the reaction was cooled to room temperature, it was diluted with 10 mL of ethyl acetate, transferred to a separatory funnel and washed three times with saturated brine, the aqueous layer was extracted once with ethyl acetate, the organic phases were combined, dried with anhydrous sodium sulfate, filtered, and the filtrate Rotary evaporation, removal of solvent, silica gel column chromatography for the residue, sequential washing with a mixed solution of petroleum ether and ethyl acetate with a volume ratio of 10:1 and 5:1, the effluent was collected according to the actual grad...

specific Embodiment 2

[0025] Specific example two: 51.5 mg (0.2 mmol) N-(2-methylthio-phenyl) p-toluamide, 61.3 mg (0.6 mmol) phenylacetylene, 10.8 mg (0.02 mmol) Ni(dppp) Cl 2 , 42.4 mg (0.4 mmol) of anhydrous sodium carbonate was added to 2 mL of dimethyl sulfoxide solvent. Three pumps and three links in an oxygen atmosphere, after plugging in an oxygen balloon, at 140 o C oil bath was reacted for 24 hours. After the reaction was cooled to room temperature, it was diluted with 10 mL of ethyl acetate, transferred to a separatory funnel and washed three times with saturated brine, the aqueous layer was extracted once with ethyl acetate, the organic phases were combined, dried over anhydrous sodium sulfate, and filtered. The filtrate was rotary evaporated, the solvent was removed, and the residue was subjected to silica gel column chromatography, followed by washing with a mixed solution of petroleum ether and ethyl acetate with a volume ratio of 10:1 and 5:1, and the effluent was collected accord...

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Abstract

The invention relates to a preparation method of a sulfur-containing 3-arylmethylene isoindolinone derivative. The method comprises the following steps: taking N-(8-quinolyl)Ar amide and aryl terminal alkyne A' as substrates, adding a catalyst, alkali and an oxidizing agent in the substrates, and in a reaction solvent, stirring the materials for a reaction for 24 h at the temperature of 140 DEG C; wherein Ar is one of phenyl, 4-methyl phenyl, 4-methoxyphenyl, 4-fluorophenyl, 4-chlorophenyl, 3-chlorophenyl, 4-bromophenyl, 4-nitro phenyl, 4-biphenyl, and 2-thienyl; and Ar' is one of 4-methyl phenyl, 4-methoxyphenyl, 4-fluorophenyl, 4-chlorophenyl, 4-bromophenyl, 4-nitro phenyl, and 4-benzotrifluoride; and obtaining a target product after the reaction is completed. The preparation method has the advantages of simple process and novel product structure, a special apparatus or a mode is not required, and the method has the advantages of simple operation, easy acquisition of the product and good yield.

Description

technical field [0001] The invention relates to the technical field of sulfur-containing 3-arymethylene isoindolinone compounds, in particular to a method for preparing sulfur-containing 3-arymethylene isoindolinone derivatives. Background technique [0002] 3-methylene isoindolinone is an important structural unit in many drugs and bioactive molecules, and can refer to "Bioorganic Medicinal Chemistry Communication" 2002 No. 12, page 3557 ( Bioorg . Med . Chems . Lett . 2002, 12 ,3557). Some of their analogues can be used as PDE4 inhibitors, you can refer to "Drug Design and Discovery", No. 11, 2014, page 1188 ( Lett. Drug. Des. Discov. 2014 , 11, 1188), antineoplastic drugs, etc., you can refer to "Natural Product Impurities" 2009 No. 72, page 1279 ( J. Nat. Prod. 2009 , 72, 1279). Therefore, the synthesis of 3-methyleneisoindolinone has attracted extensive attention of researchers, and various synthetic strategies for the construction of these heterocycles ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D209/46C07D495/04
CPCC07D209/46C07D495/04
Inventor 张小红张兴国邓辰亮胡伯伦
Owner WENZHOU UNIVERSITY
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