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Method for preparing 2-alkylthioquinoline derivatives

A technology for alkylthioquinoline and derivatives, which is applied in the field of preparing 2-alkylthioquinoline derivatives, can solve the problems of low yield of 2-alkylthioquinoline derivatives and the like, and achieves easy purification and synthesis of products. High rate, scientific and reasonable synthesis method

Inactive Publication Date: 2015-11-18
TSINGHUA UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

No matter whether it is industrial production or preparation of quinoline in the laboratory, the yield of the resulting 2-alkylthioquinoline derivatives is very low

Method used

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  • Method for preparing 2-alkylthioquinoline derivatives
  • Method for preparing 2-alkylthioquinoline derivatives
  • Method for preparing 2-alkylthioquinoline derivatives

Examples

Experimental program
Comparison scheme
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Embodiment 1

[0038] Embodiment one, 2-methylthio-3,4-diphenyl-quinoline (R in structural formula I 1 =R 2 = phenyl, R = hydrogen, R 3 = methyl)

[0039] In the reactor of 25mL, add successively compound phenylisothiocyanate (0.75mmol, 90 μ L) shown in formula II, compound tolan (0.5mmol, 89mg) shown in formula III, methyl trifluoromethanesulfonate ( 1.5mmol, 172μL), and finally add 1.5mL of dichloroethane as a solvent, seal the reactor, and react at 130°C for 12h. After the reaction system was cooled, 15 mL of water and 15 mL of dichloromethane were added and stirred for 30 min, then extracted three times with 15 mL of dichloromethane, and the organic phases were combined. The organic phase was washed with saturated brine, and finally dried over anhydrous magnesium sulfate for 0.5 h. After filtration, the organic phase was rotary evaporated to obtain a crude product. The crude product was separated by column chromatography with petroleum ether: ether: triethylamine = 200:5:0.5 (volume ...

Embodiment 2

[0044] Embodiment two, 2-methylthio-4-phenyl-quinoline (R in structural formula I 1 = Hydrogen, R 2 = phenyl, R = hydrogen, R 3 = methyl)

[0045] Into a 25 mL reactor, phenylisothiocyanate (0.75 mmol, 90 μL), phenylacetylene (0.5 mmol, 55 μL), methyl trifluoromethanesulfonate (1.5 mmol, 172 μL) were sequentially added, and finally 1.5 mL of di Ethyl chloride was used as a solvent, the reactor was sealed, and reacted at 130°C for 12h. After the reaction system was cooled, 15 mL of water and 15 mL of dichloromethane were added and stirred for 30 min, then extracted three times with 15 mL of dichloromethane, and the organic phases were combined. The organic phase was washed with saturated brine, and finally dried over anhydrous magnesium sulfate for 0.5 h. After filtration, the organic phase was rotary evaporated to obtain a crude product. The crude product was separated by column chromatography with petroleum ether: ether: triethylamine=200:5:0.5 (volume ratio) as the eluen...

Embodiment 3

[0050] Embodiment three, 2-methylthio-3-methyl-4-phenyl-quinoline (R in structural formula I 1 = methyl, R 2 = phenyl, R = hydrogen, R 3 = methyl)

[0051] To a 25mL reactor, add phenylisothiocyanate (0.75mmol, 90μL), 1-phenyl-1-propyne (0.5mmol, 68μL), methyl trifluoromethanesulfonate (1.5mmol, 172μL) in sequence ), and finally add 1.5mL dichloroethane as a solvent, seal the reactor, and react at 130°C for 12h. After the reaction system was cooled, 15 mL of water and 15 mL of dichloromethane were added and stirred for 30 min, then extracted three times with 15 mL of dichloromethane, and the organic phases were combined. The organic phase was washed with saturated brine, and finally dried over anhydrous magnesium sulfate for 0.5 h. After filtration, the organic phase was rotary evaporated to obtain a crude product. The crude product was separated by column chromatography with petroleum ether: ether: triethylamine=200:5:0.5 (volume ratio) as the eluent and 200-300 mesh sili...

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Abstract

The invention discloses a preparation method of a 2-alkylsulfenylquinoline derivative. The method comprises the following steps of sequentially adding a compound as shown in the formula II, a compound as shown in the formula III and trifluoromethanesulfonie ester into a reaction vessel, then, adding a solvent, uniformly mixing the solution, and carrying out continuous electrophilic reaction to obtain the 2-alkylsulfenylquinoline derivative as shown in the formula I. The method is scientific and reasonable and capable of synthesizing the 2-alkylsulfenylquinoline derivative which can not be synthesized by using other methods; moreover, the preparation method also has the characteristics of high synthesis yield, good selectivity, easy product purification, no any metal introduction in the synthesis process and the like.

Description

technical field [0001] The invention relates to a method for preparing 2-alkylthioquinoline derivatives. Background technique [0002] Quinoline, also known as benzopyridine and azine, is a heterocyclic aromatic organic compound with strong aromaticity. The benzene ring part is prone to electrophilic substitution reactions at the 5 and 8 positions, and it is easy to generate 5, 8-substituted quinoline derivatives. Quinoline and its derivatives are important fine chemical raw materials, mainly used in the synthesis of medicines, dyes, pesticides and various chemical auxiliaries. Many quinoline compounds are important pharmaceutical intermediates, and many new drugs containing quinoline rings have been continuously developed in recent years. Quinoline itself was originally distilled from the antimalarial drug quinine. Quinoline and quinoline derivatives such as 2-alkylthioquinoline derivatives can also be used to synthesize acid dye yellow 3, direct yellow 22, solvent yellow...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D215/36C07D221/08C07D215/54
CPCC07D215/36C07D215/54C07D221/08
Inventor 席婵娟赵鹏
Owner TSINGHUA UNIV
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