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Preparation method of 7-chloro-6H-benzopyran[4,3-b]quinoline and derivative thereof

A technology of benzopyran and its derivatives, which is applied in pharmaceutical and chemical intermediates and related chemical fields, can solve problems such as harsh conditions, cumbersome steps, and complicated operations, and achieve the effects of mild conditions, simple operations, and high yields

Inactive Publication Date: 2015-02-04
DALIAN UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the method has cumbersome steps, harsh conditions, complicated operation, and the cumulative yield is only 12%, which is inconsistent with the concept of "atom economy" pursued by people.

Method used

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  • Preparation method of 7-chloro-6H-benzopyran[4,3-b]quinoline and derivative thereof
  • Preparation method of 7-chloro-6H-benzopyran[4,3-b]quinoline and derivative thereof
  • Preparation method of 7-chloro-6H-benzopyran[4,3-b]quinoline and derivative thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] Example 1: Synthesis of 7-chloro-6H-benzopyrano[4,3-b]quinoline (1a)

[0035]

[0036] 2-propargyloxy-N-benzylidene aniline (4.2mg, 0.2mmol), cuprous oxide (0.3mg, 0.002mmol), 2,3,5,6-tetrachloro-p-benzoquinone (49.0mg, 0.2 mmol) and sodium chloride (5.8mg, 0.1mmol) were sequentially added into the Schlenk reaction flask, and after vacuum and nitrogen replacement for 3 times, 0.01mL of ethylene glycol dimethyl ether was added in a nitrogen atmosphere and reacted at 30°C for 4 hours. After the reaction, the solvent was removed under reduced pressure and separated by column chromatography (eluent: petroleum ether: ethyl acetate = 20:1, V:V) to obtain 0.048 g of a light yellow solid product with a yield of 87%. Mp 143-145°C; 1 H-NMR (400MHz, CDCl 3 )δ8.41(d, J=6.4Hz, 1H), 8.10(dd, J=8.4, 17.2Hz, 2H), 7.71(dd, J=7.2, 8.0Hz, 1H), 7.55(dd, J=3.2 ,15.2Hz,1H),7.36(dd,J=7.6,15.2Hz,1H),7.13(dd,J=7.6,15.2Hz,1H),6.99(d,J=8.0Hz,1H),5.49(s ,2H); 13 C-NMR (100MHz, CDCl 3 )δ15...

Embodiment 2

[0037] Example 2: Synthesis of 11-methyl-7-chloro-6H-benzopyrano[4,3-b]quinoline (1b)

[0038]

[0039] 2-propargyloxy-N-(2-methyl)-benzylidene aniline (50.0mg, 0.2mmol), cuprous iodide (1.9mg, 0.01mmol), 2,3,5,6-tetrachloro P-benzoquinone (980.0mg, 4.0mmol) and potassium chloride (14.9mg, 0.2mmol) were added to the Schlenk reaction flask in turn, and after vacuum and nitrogen replacement for 3 times, in a nitrogen atmosphere, 0.5mL of acetonitrile was added, and the reaction was carried out at 60°C After 6 hours of reaction, the solvent was removed under reduced pressure and separated by column chromatography (eluent: petroleum ether: ethyl acetate = 20:1, V:V) to obtain 0.045 g of a light yellow solid product with a yield of 81%. Mp 104-106°C; 1 H-NMR (400MHz, CDCl 3 )δ8.49(d, J=8.0Hz, 1H), 8.01(d, J=7.6Hz, 1H), 7.57(d, J=6.8Hz, 1H), 7.46(dd, J=8.0, 7.6Hz, 1H),7.38(dd,J=7.2,8.0Hz,1H),7.15(dd,J=7.2,7.6Hz,1H),7.01(d,J=8.0Hz,1H),5.53(s,2H), 2.87(s,3H); 13C-NMR (101MHz, ...

Embodiment 3

[0040] Example 3: Synthesis of 9-methyl-2-methoxy-7-chloro-6H-benzopyran[4,3-b]quinoline (1c)

[0041]

[0042] 5-methoxy-2-propargyloxy-N-(4-methyl)-benzylidene aniline (54.6mg, 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, in a nitrogen atmosphere, toluene was added 1.0 mL, reacted at 90°C for 8 hours. After the reaction, the solvent was removed under reduced pressure and separated by column chromatography (eluent: petroleum ether: ethyl acetate = 20:1, V:V) to obtain the main product of light yellow solid 0.041 g, yield 65%. Mp 144-146°C; 1 H-NMR (400MHz, CDCl 3 )δ7.99(d, J=8.8Hz, 1H), 7.90(s, 2H), 7.53(d, J=8.4Hz, 1H), 6.93(s, 2H), 5.43(s, 2H), 3.91( s,3H),2.56(s,3H); 13 C-NMR (100MHz, CDCl 3 )δ149.9, 145.9, 142.8, 141.7, 132.1, 131.3, 127.2, 124.2, 120.3, 118.0, 1...

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Abstract

The invention belongs to the technical fields of medicine chemical intermediate and related chemical technologies and relates to a preparation method of a 7-chloro-6H-benzopyran[4,3-b]quinoline compound. The 7-chloro-6H-benzopyran[4,3-b]quinoline compound is widely applied in various fields of chemistry and has a wide market prospect. In the invention, a series of 7-chloro-6H-benzopyran[4,3-b]quinoline compounds are synthesized through a Diels-Alder reaction with a Schiff base being a raw material, tetrachloro-p-benzoquinone being a chlorine source and a copper salt being a catalyst. The method is short in synthetic route, is gentle in conditions, is simple in operation and is expected to achieve industrialized production. The method is short in synthetic route, is gentle in conditions, is simple in operation, is high in yield and has large use value and socially economic benefit.

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 7-chloro-6H-benzopyrano[4,3-b]quinoline and derivatives thereof. Background technique [0002] 7-Chloro-6H-benzopyrano[4,3-b]quinoline and its derivatives are an important class of biologically active molecules, whose skeleton structure frequently appears in drug molecules, and is effective for osteoporosis, enteritis , estrogen-dependent tumors and anxiety disorders have good therapeutic effects, and have important applications in the fields of organic synthesis and medicinal chemistry. [0003] Regarding the synthesis of 7-chloro-6H-benzopyrano[4,3-b]quinoline compounds, the following methods are usually used: [0004] [0005] Using m-methoxyphenol as a raw material, 7-chloro-6H-benzopyrano[4,3-b]quinoline was finally synthesized through five steps (Bioorg.&Med.Chem.Lett.,2007,17,4053- 4056). ...

Claims

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Application Information

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IPC IPC(8): C07D491/052
CPCC07D491/052
Inventor 于晓强王娇冯秀娟包明
Owner DALIAN UNIV OF TECH
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