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A kind of preparation method of 7-chloro-6h-benzothiopyran [4,3-b] quinoline and derivatives thereof

A technology of benzothiopyran and quinoline, which is applied in the field of preparation of 7-chloro-6H-benzothiopyran[4,3-b]quinoline and derivatives thereof, can solve the problems such as the synthetic method has not yet been reported. , to achieve the effect of great use value and social and economic benefits, mild conditions, and good anti-hepatitis B virus efficacy

Active Publication Date: 2017-05-03
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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  • A kind of preparation method of 7-chloro-6h-benzothiopyran [4,3-b] quinoline and derivatives thereof
  • A kind of preparation method of 7-chloro-6h-benzothiopyran [4,3-b] quinoline and derivatives thereof
  • A kind of preparation method of 7-chloro-6h-benzothiopyran [4,3-b] quinoline and derivatives 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 (53.2 mg, 0.2 mmol), cuprous oxide (0.3 mg, 0.002 mmol), 2,3,5,6-tetrachlorop-benzoquinone (49.0 mg, 0.2 mmol) and sodium chloride (5.8 mg, 0.1 mmol) were successively added to the Schlenk reaction flask, after vacuum and nitrogen replacement 3 times, in a nitrogen atmosphere, 0.01 mL of ethylene glycol dimethyl ether was added, 30 The reaction was carried out at °C for 4 hours. After the reaction was completed, the solvent was removed under reduced pressure and separated by column chromatography (eluent: petroleum ether: ethyl acetate=20:1, V:V) to obtain 49 mg of light yellow solid product, yield 82% . Mp 149-150℃; 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 ...

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)-benzylideneaniline (60.0 mg, 0.2 mmol), cuprous iodide (1.9 mg, 0.01 mmol), 2,3,5, 6-Tetrachloro-p-benzoquinone (980.0 mg, 4.0 mmol) and potassium chloride (14.9 mg, 0.2 mmol) were successively added to the Schlenk reaction flask, and after three times of vacuum and nitrogen replacement, 0.5 mL of acetonitrile was added in a nitrogen atmosphere , 60 ℃ of reaction for 6 hours, after the reaction, the solvent was removed under reduced pressure, column chromatography separation (eluent is petroleum ether: ethyl acetate = 20:1, V:V) to obtain a light yellow solid main product 50.0mg, Yield 84%. Mp 166-168℃; 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); 13 C-NMR (100MHz, CDCl 3)δ153.0,146.0,...

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)-benzylideneaniline (78.4 mg, 0.2 mmol), cuprous bromide (2.9 mg, 0.02 mmol), 2,3,5, 6-Tetrachloro-p-benzoquinone (148.0 mg, 6.0 mmol) and calcium chloride (44.4 mg, 0.4 mmol) were added to the Schlenk reaction flask in turn. After 3 times of vacuum and nitrogen replacement, 1.0 mL 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, and column chromatography was performed (eluent was petroleum ether: ethyl acetate=20:1, V:V) to obtain a light yellow solid main product 63.0mg, Yield 72%. Mp 203-205℃; 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 (100MHz, CDCl 3 )δ153.2,1...

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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 chemical intermediates and related chemical technologies, and relates to a preparation method of a new 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, which have good anti-hepatitis B virus efficacy and have important applications in the fields of organic synthesis and medicinal chemistry. However, its skeleton structure is 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 one of the benzothiopyran[4,3-b]quinoline derivatives. Due to its halogen group, it can be obtained by Further transformation to generate various types of benzothiopyran[4,3-b]quinoline derivatives, the development of 7-chloro-6H-benzothiopyran[4,3-b]quinoline,...

Claims

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Application Information

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Patent Type & Authority Patents(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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