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Synthetic method for 2-aliphatic sulfonyl quinoline derivative

The technology of a family of sulfonylquinolines and synthesis methods is applied in the field of synthesis of 2-aliphatic sulfonylquinolines, which can solve the problems of harsh reaction conditions, increased operation steps, and high cost of raw materials in the synthesis method, so as to avoid environmental problems and reduce impact , the effect of low price

Inactive Publication Date: 2019-01-04
CENT SOUTH UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] 1) Sodium aliphatic sulfinate is used as a sulfonylation reagent. It is necessary to reduce the corresponding aliphatic sulfonyl chloride to prepare sodium aliphatic sulfinate under alkaline conditions in advance, and then separate and purify, which increases the operation steps and the cost of raw materials is higher ;
[0007] 2) The reaction conditions of the synthesis method are harsh, and high-temperature microwave radiation is required to promote the reaction;
[0008] 3) Using expensive and toxic dimethyl sulfoxide as a solvent not only has high reaction costs but also causes side effects to the environment

Method used

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  • Synthetic method for 2-aliphatic sulfonyl quinoline derivative
  • Synthetic method for 2-aliphatic sulfonyl quinoline derivative
  • Synthetic method for 2-aliphatic sulfonyl quinoline derivative

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] 2-Benzylsulfonylquinoline:

[0036]

[0037] In a 50mL round-bottomed flask, add 1.64g of 2-chloroquinoline, 2.10g of benzylsulfonyl chloride, 2.09g of potassium sulfite, and 20ml of water in sequence, and react ultrasonically for 10 minutes in a 60W / 160KHz ultrasonic reaction device. The crude product of 2-benzylsulfonylquinoline was obtained by filtration, and the crude product was washed with 95% ethanol to obtain 2.60 g of the corresponding pure product, with a yield of 92%. NMR data:

[0038] 1 H NMR (400MHz, CDCl 3 ):δ=8.32–8.28(m,2H),7.92–7.86(m,3H),7.73(t,J=8.0Hz,1H),7.24–7.19(m,5H),4.80(s,2H); 13 C NMR (100MHz, CDCl 3 ): δ=156.2, 147.1, 138.4, 131.2, 131.1, 130.1, 129.3, 129.1, 128.6, 128.6, 127.9, 127.4, 117.9, 58.2.

[0039] Control group 1:

[0040] Replace ultrasonic-assisted reactions with room temperature stirred reactions:

[0041] In a 50 mL round bottom flask, 1.64 g of 2-chloroquinoline, 2.10 g of benzylsulfonyl chloride, 2.09 g of potassium...

Embodiment 2

[0067] 2-bromoquinoline is the synthesis of 2-benzylsulfonylquinoline as raw material:

[0068] In a 50mL round-bottom flask, add 2.08g of 2-bromoquinoline, 2.10g of benzylsulfonyl chloride, 2.09g of potassium sulfite, 20ml of water, and react ultrasonically for 10 minutes in a 60W / 160KHz ultrasonic reaction device. The crude product of 2-benzylsulfonylquinoline was obtained by filtration, and the crude product was washed with 95% ethanol to obtain 2.57 g of the corresponding pure product, with a yield of 92%.

Embodiment 3

[0070] 2-iodoquinoline is the synthesis of 2-benzylsulfonylquinoline as raw material:

[0071] In a 50mL round-bottomed flask, add 2.55g of 2-iodoquinoline, 2.10g of benzylsulfonyl chloride, 2.09g of potassium sulfite, 20ml of water, and react ultrasonically for 10 minutes in a 60W / 160KHz ultrasonic reaction device. 2-benzylsulfonylquinoline was obtained by filtration: the crude product was washed with 95% ethanol to obtain 2.60 g of the corresponding pure product with a yield of 92%.

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Abstract

The invention discloses a synthetic method for a 2-aliphatic sulfonyl quinoline derivative. Under the action of ultrasound, 2-halogenated quinoline, an aliphatic sulfonyl chloride compound and sulfitereact in one pot in an aqueous solution, to synthesize the 2-aliphatic sulfonyl quinoline derivative. The method disclosed by the invention is readily available in raw materials, simple in reaction conditions, mild in reaction, green and energy-saving, high in reaction selectivity and yield, and excellent in compatibility of substrate functional groups, in particular, by adopting the synthetic method for the 2-aliphatic sulfonyl quinoline derivative, the 2-aliphatic sulfonyl quinoline derivative product can be directly separated by filtration, so that the production cost is lowered, furthermore, the problem of environmental pollution in the traditional method is further avoided. The synthetic method for the 2-aliphatic sulfonyl quinoline derivative disclosed by the invention is environmentally friendly and higher in application values.

Description

technical field [0001] The invention relates to a method for synthesizing 2-aliphatic sulfonylquinoline, in particular to a multi-component one-pot reaction synthesis of 2-haloquinoline, aliphatic sulfonyl chloride compound and sulfite assisted by ultrasound in the aqueous phase A method for 2-aliphatic sulfonylquinoline derivatives belongs to the technical field of organic intermediate synthesis. Background technique [0002] 2-Aliphatic sulfonylquinoline is an important class of quinoline derivatives, which play an important role in many fields such as organic synthesis and drug development. The coupling reaction of 2-haloquinoline and sodium sulfinate is the most regioselective method for synthesizing 2-sulfonylquinoline, compared to 2-arylsulfonylquinoline and its derivatives which are more researched Synthetic method of compound, utilize easily available 2-haloquinoline as raw material, the method for synthesizing 2-aliphatic sulfonylquinoline is only an example. [0...

Claims

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Application Information

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IPC IPC(8): C07D215/36
CPCC07D215/36
Inventor 肖芳肖元元吴心音张玉静
Owner CENT SOUTH UNIV
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