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Preparation methods of 7-chlorine-6H-benzothiapyran [4,3-b] quinoline and derivative thereof

A technology for benzothiopyran and derivatives, which is applied to pharmaceutical chemical intermediates and related chemical fields, can solve problems such as the synthesis method that has not yet been reported, achieve great use value, social and economic benefits, good anti-hepatitis B virus curative effect, and simple operation. Effect

Active Publication Date: 2015-01-07
DALIAN UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, as a new compound, 7-chloro-6H-benzothiopyran [4,3-b] quinoline has not been reported so far.

Method used

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  • Preparation methods of 7-chlorine-6H-benzothiapyran [4,3-b] quinoline and derivative thereof
  • Preparation methods of 7-chlorine-6H-benzothiapyran [4,3-b] quinoline and derivative thereof
  • Preparation methods of 7-chlorine-6H-benzothiapyran [4,3-b] quinoline and derivative thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] Example 1: Synthesis of 2-methyl-7-chloro-6H-benzothiopyran[4,3-b]quinoline (1a)

[0033]

[0034] 5-methyl-2-propargylthio-N-benzylidene aniline (53.2mg, 0.2mmol), cuprous oxide (0.3mg, 0.002mmol), 2,3,5,6-tetrachloro-p-benzoquinone (49.0mg, 0.2mmol), sodium chloride (5.8mg, 0.1mmol) were successively added into the Schlenk reaction flask, and after vacuum and nitrogen replacement three times, in a nitrogen atmosphere, 0.01mL of ethylene glycol dimethyl ether was added, 30 After reaction at ℃ for 4 hours, after the reaction, the solvent was removed under reduced pressure, separated by column chromatography (eluent: petroleum ether: ethyl acetate = 20:1, V:V), and 49 mg of light yellow solid product was obtained with a yield of 82%. . Mp 149-150°C; 1 H-NMR (400MHz, CDCl 3 )δ8.37(s,1H),8.18(d,J=8.4Hz,1H),8.13(d,J=8.4Hz,1H),7.72(dd,J=8.0,8.4Hz,1H),7.58( dd,J=8.0,7.2Hz,1H),7.29(d,J=7.6Hz,1H),7.15(d,J=7.6Hz,1H),4.30(s,1H),2.44(s,3H); 13 C-NMR (100MHz, CDCl 3 )δ152....

Embodiment 2

[0035] Example 2: Synthesis of 2-methyl-7,9-dichloro-6H-benzothiopyran[4,3-b]quinoline (1b)

[0036]

[0037] 5-Methyl-2-propargylthio-N-(4-chloro)-benzylidene aniline (60.0mg, 0.2mmol), cuprous iodide (1.9mg, 0.01mmol), 2,3,5, 6-Tetrachloro-p-benzoquinone (980.0mg, 4.0mmol) and potassium chloride (14.9mg, 0.2 mmol) were successively added to the Schlenk reaction flask, and after vacuum and nitrogen replacement for 3 times, in a nitrogen atmosphere, 0.5mL of acetonitrile was added , reacted at 60°C for 6 hours, after the reaction was completed, the solvent was removed under reduced pressure, separated by column chromatography (eluent was petroleum ether: ethyl acetate = 20:1, V:V), and 50.0 mg of the main product was obtained as a light yellow solid, Yield 84%. Mp 166-168°C; 1 H-NMR (400MHz, CDCl 3 )δ8.35(d, J=1.2Hz, 1H), 8.19(d, J=2.4Hz, 1H), 8.08(d, J=8.8Hz, 1H), 7.67(dd, J=2.4, 8.8Hz, 1H), 7.31(d, J=7.6Hz, 1H), 7.18(dd, J=1.6, 8.0Hz, 1H), 4.31(s, 2H), 2.45(s, 3H); 1...

Embodiment 3

[0038] Example 3: Synthesis of 2-methyl-7-chloro-9-iodo-6H-benzothiopyran[4,3-b]quinoline (1c)

[0039]

[0040] 5-methyl-2-propargylthio-N-(4-iodo)-benzylidene aniline (78.4mg, 0.2mmol), cuprous bromide (2.9mg, 0.02mmol), 2,3,5, 6-Tetrachloro-p-benzoquinone (148.0mg, 6.0mmol) and calcium chloride (44.4mg, 0.4mmol) were successively added to the Schlenk reaction flask, and after vacuum and nitrogen replacement for 3 times, 1.0mL of toluene was added in a nitrogen atmosphere , reacted at 90°C for 8 hours, after the reaction was completed, the solvent was removed under reduced pressure, separated by column chromatography (eluent was petroleum ether: ethyl acetate = 20:1, V:V), and 63.0 mg of the main product was obtained as a light yellow solid. Yield 72%. Mp 203-205°C; 1 H-NMR (400MHz, CDCl 3 )δ8.58(d, J=1.6Hz, 1H), 8.35(d, J=1.2Hz, 1H), 7.96(dd, J=2.0, 8.8Hz, 1H), 7.84(d, J=8.8Hz, 1H), 7.39(d, J=8.0Hz, 1H), 7.18(dd, J=1.6, 8.0Hz, 1H), 4.30(s, 2H), 2.45(s, 3H); 13 C-NMR...

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Abstract

The invention belongs to the pharmaceutical chemical engineering intermediates and relative chemical technical field and relates to preparation methods of 7-chlorine-6H-benzothiapyran [4,3-b] quinoline and a derivative thereof. Benzothiapyran [4,3-b] quinoline is an important bioactive molecule, has good curative efficacy of resisting hepatitis B virus and has an important application in the fields of organic synthesis, medicinal chemistry and the like. The 7-chlorine-6H-benzothiapyran [4,3-b] quinoline is one of derivatives of benzothiapyran [4,3-b] quinoline, and a synthetic method of 7-chlorine-6H-benzothiapyran [4,3-b] quinoline is not reported yet so far. The 7-chlorine-6H-benzothiapyran [4,3-b] quinoline is prepared by the following steps: with a schiff base derivative as a raw material, carrying out Diels-Alder reaction under the actions of salt, chloranil and a metal copper compound catalyst to generate the 7-chlorine-6H-benzothiapyran [4,3-b] quinoline. The preparation methods have the advantages of short synthesis rout, mild conditions, high yield and the like, is simple to operate and have large use value and social and economic benefits.

Description

technical field [0001] The invention belongs to the field of pharmaceutical and chemical intermediates and related chemical technologies, and relates to a preparation method of a novel compound 7-chloro-6H-benzothiopyran[4,3-b]quinoline and derivatives thereof. Background technique [0002] Benzothiopyran[4,3-b]quinoline compounds are a class of important biologically active molecules with good anti-hepatitis B virus efficacy, and have important applications in the fields of organic synthesis and medicinal chemistry. However, its skeleton structure is relatively complex and its synthesis is difficult, so benzothiopyran [4,3-b] quinoline derivatives have not been effectively developed. 7-Chloro-6H-benzothiopyran [4,3-b] quinoline is a kind of benzothiopyran [4,3-b] quinoline derivatives, because it has a halogen group, it can pass Further transformation to generate various types of benzothiopyran [4,3-b] quinoline derivatives, the development of 7-chloro-6H-benzothiopyran [4...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D495/04
CPCC07D495/04
Inventor 于晓强王娇冯秀娟包明
Owner DALIAN UNIV OF TECH
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