Benzene ring fused 5/6/7/6 tetracyclic compound and synthesis method thereof

A tetracyclic compound and synthetic method technology, applied in the field of organic compound synthesis, can solve the problems of low yield and cumbersome reaction steps, and achieve the effects of high yield, single stereoselectivity, and simple operation

Active Publication Date: 2022-06-07
NANJING FORESTRY UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] At present, most of the methods for synthesizing benzene ring-fused 6/7/6 tricyclic skel

Method used

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  • Benzene ring fused 5/6/7/6 tetracyclic compound and synthesis method thereof
  • Benzene ring fused 5/6/7/6 tetracyclic compound and synthesis method thereof
  • Benzene ring fused 5/6/7/6 tetracyclic compound and synthesis method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] Take a 10mL round-bottomed flask, add o-alkynylbenzaldehyde 2a (0.2mmol), Molecular sieves (100 mg) and platinum dibromide catalyst (0.01 mmol) were added to tetrahydrofuran (2 mL) under an argon atmosphere, and the reaction was carried out at 70° C. for 12 hours. After cooling to room temperature, tetrabutylammonium tribromide (0.01 mmol) was added to the reaction system, and methanol (2 ml) was further reacted for 1 hour. After the reaction, the insolubles were removed by filtration, water and ethyl acetate were added for extraction twice, the organic phases were combined, dried over anhydrous magnesium sulfate, the filtrate was filtered and concentrated by rotary evaporation, and the crude product was separated by silica gel column chromatography with a volume ratio of 25: The 2-25:8 mixed solution of petroleum ether and ethyl acetate was used as the eluent for gradient elution to obtain 40.2 mg of the target product 1a.

[0035] The reaction equation is:

[0036]...

Embodiment 2

[0044] Take a 10mL round-bottomed flask, add o-alkynylbenzaldehyde 2b (0.2mmol), Molecular sieves (100 mg) and platinum dibromide catalyst (0.01 mmol) were added to tetrahydrofuran (2 mL) under argon atmosphere, and the reaction was carried out at 70° C. for 12 hours. After cooling to room temperature, tetrabutylammonium tribromide (0.01 mmol) was added to the reaction system, and methanol (2 ml) was further reacted for 1 hour. After the reaction, the insolubles were removed by filtration, water and ethyl acetate were added for extraction twice, the organic phases were combined, dried over anhydrous magnesium sulfate, the filtrate was filtered and concentrated by rotary evaporation, and the crude product was separated by silica gel column chromatography with a volume ratio of 25: A mixed solution of petroleum ether and ethyl acetate in a ratio of 1 to 25:6 was used as the eluent for gradient elution to obtain 57.5 mg of the target product 1b.

[0045] The reaction equation i...

Embodiment 3

[0051] Take a 10mL round-bottomed flask, add o-alkynylbenzaldehyde 2c (0.2mmol), Molecular sieves (100 mg) and platinum dibromide catalyst (0.01 mmol) were added to tetrahydrofuran (2 mL) under argon atmosphere, and the reaction was carried out at 70° C. for 12 hours. After cooling to room temperature, tetrabutylammonium tribromide (0.01 mmol) was added to the reaction system, and methanol (2 ml) was further reacted for 1 hour. After the reaction, the insolubles were removed by filtration, water and ethyl acetate were added for extraction twice, the organic phases were combined, dried over anhydrous magnesium sulfate, the filtrate was filtered and concentrated by rotary evaporation, and the crude product was separated by silica gel column chromatography with a volume ratio of 25: A 1-5:1 mixed solution of petroleum ether and ethyl acetate was used as the eluent for gradient elution to obtain 59.7 mg of the target product 1c.

[0052] The reaction equation is:

[0053]

...

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Abstract

The invention discloses a benzene ring-fused 5/6/7/6 tetracyclic compound and a synthesis method thereof, and the benzene ring-fused 5/6/7/6 tetracyclic compound is obtained by taking an o-alkynyl benzaldehyde compound connected with cyclohexadienone propargyl ether as a raw material, carrying out heating reaction in a solvent tetrahydrofuran under the catalysis of a platinum catalyst, and carrying out post-treatment. The invention provides a novel synthesis method of a benzene ring fused 5/6/7/6 tetracyclic compound which is not easy to prepare by a conventional method, four continuous chiral centers can be constructed in one step, and the compound has excellent stereoselectivity; the method has the advantages of simplicity in operation, wide substrate range, high yield and the like.

Description

technical field [0001] The invention belongs to the technical field of organic compound synthesis, in particular to a benzene ring-fused 5 / 6 / 7 / 6 tetracyclic compound and a synthesis method thereof. Background technique [0002] The benzene ring-fused 6 / 7 / 6 tricyclic skeleton is an important building block for many natural product molecules, and studies have shown that these compounds have diverse biological activities, such as antibacterial, antifungal, antioxidant and anticancer activities. For example, the natural product (-)-Barbatusol extracted from the root of Coleus serrata can be used to treat high blood pressure, and the natural product Fruticulin A extracted from Salvia has anti-inflammatory and labor pain effects. Pisiferin extracted from leaves has good cytotoxicity to cancer cells, (+)-Rosmaridiphenol is a rosmarinol isolated from rosemary leaves and has strong antioxidant properties. Taxamairin H was the first terpenoid isolated from the stem bark of Taxus chin...

Claims

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Application Information

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IPC IPC(8): C07D307/77C07D493/06C07D493/08
CPCC07D307/77C07D493/06C07D493/08C07B2200/13Y02A50/30
Inventor 饶卫东胡睿王泽梁陈继超
Owner NANJING FORESTRY UNIV
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