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Method for preparing 6H-benzo[C]benzopyran compound

A technology for benzopyran and compounds, applied in the field of preparing 6H-benzo[C]benzopyran compounds

Active Publication Date: 2015-05-13
TAIZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In recent years, many subjects have combined 6H-benzo[C]benzopyran compounds (J.Am.Chem.Soc.2004; J.Org.Chem.2005,70,7578; Org.Lett.2005, 7,1857; Chem.Eur.J.2011,17,3596; Chem.Eur.J.2012,18,4859), but the synthesis of functionalized 6H-benzo[C]benzopyran compounds is still a research challenge

Method used

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  • Method for preparing 6H-benzo[C]benzopyran compound
  • Method for preparing 6H-benzo[C]benzopyran compound
  • Method for preparing 6H-benzo[C]benzopyran compound

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Experimental program
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Effect test

Embodiment 1

[0016] In a 20mL dry reaction tube, 2-hydroxy-2'-bromobiphenyl (0.5mmol), triphenylphosphine (0.1mmol), and 1.5mL of acetonitrile were heated to 80-85 degrees Celsius under a nitrogen protection system ( Such as 85 degrees Celsius), dropwise added methyl propiolate (0.55mmol), magnetically stirred for 2 hours, then added Pd(dppf)Cl 2 (0.025mmol), tetrabutylammonium chloride (0.5mmol), sodium carbonate (1.0mmol), and then react for 6-10 hours (for example, 8 hours), TLC detection, raw materials disappear, add appropriate amount of water to dissolve, and dichloromethane The reaction solution was extracted, the organic phases were combined, the organic solvent was concentrated, and the product was further purified by column chromatography with a yield of 80%.

[0017] (E)-6H-Benzo[c]chromen-6-ylidene acetate methyl ester

[0018] 1 H NMR (400MHz, CDCl 3 ): δ=7.96(d, J=8.0Hz, 1H), 7.88(d, J=8.0Hz, 1H), 7.77(d, J=8.0Hz, 1H), 7.58-7.54(m, 1H), 7.41 -7.32(m,3H),7.19(m,1H),5.85(s,...

Embodiment 2

[0020] In a 20mL dry reaction tube, 3-methyl-2-hydroxy-2'-bromobiphenyl (0.5mmol), triphenylphosphine (0.1mmol), and 1.5mL of acetonitrile were heated to 80-85°C (e.g. 85°C), add methyl propiolate (0.55mmol) dropwise, stir magnetically for 2 hours, then add Pd(dppf)Cl 2 (0.025mmol), tetrabutylammonium chloride (0.5mmol), sodium carbonate (1.0mmol), and then react for 6-10 hours (for example, 8 hours), TLC detection, raw materials disappear, add appropriate amount of water to dissolve, and dichloromethane The reaction solution was extracted, the organic phases were combined, the organic solvent was concentrated, and the product was further purified by column chromatography with a yield of 63%.

[0021] (E)-4-Methyl-6H-benzo[c]benzopyran-6-ylidenyl acetate methyl ester

[0022] 1 H NMR (400MHz, CDCl 3): δ=7.96(d, J=7.6Hz, 1H), 7.78(d, J=7.6Hz, 1H), 7.72(d, J=7.6Hz, 1H), 7.58-7.53(m, 1H), 7.40 -7.36(m,1H),7.26-7.22(m,1H),7.08(t,J=7.6Hz,1H),5.86(s,1H),3.80(s,3H),2.56(s,3H); 1...

Embodiment 3

[0024] In a 20mL dry reaction tube, 2-hydroxy-4',5'-dimethyl-2'-bromobiphenyl (0.5mmol), triphenylphosphine (0.1mmol), acetonitrile 1.5mL, under nitrogen protection Under the system, the temperature was raised to 85 degrees Celsius, methyl propiolate (0.55 mmol) was added dropwise, magnetically stirred for 2 hours, and then Pd(dppf)Cl was added 2 (0.025mmol), tetrabutylammonium chloride (0.5mmol), sodium carbonate (1.0mmol), reacted again for 8 hours, TLC detection, raw material disappears, add appropriate amount of water to dissolve, extract reaction solution with dichloromethane, combine organic phase , concentrated the organic solvent, and further purified by column chromatography to obtain the product with a yield of 85%.

[0025] (E)-7,8-Dimethyl-6H-benzo[c]benzopyran-6-ylidenyl acetate methyl ester

[0026] 1 H NMR (400MHz, CDCl 3 ):δ=7.87(d, J=8.0Hz, 1H), 7.72(s, 1H), 7.54(s, 1H), 7.35-7.32(m, 2H), 7.20-7.15(m, 1H), 5.81( s,1H),3.78(s,3H),2.38(s,3H),2.33(s,3H); 13 ...

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Abstract

The invention discloses a method for preparing a 6H-benzo[C]benzopyran compound. The method comprises the following step of reacting a 2-hydroxy-2'-bromobiphenyl compound and a propiolate compound serving as raw materials for 10 hours in the presence of triphenylphosphine, metal palladium, tetrabutylammonium chloride and sodium carbonate, by adopting acetonitrile serving as a solvent and in nitrogen protection system at a reaction temperature of 85 DEG C to synthesize the target compound. The method is simple, high in yield and mild in conditions and has good application prospects.

Description

technical field [0001] The invention relates to an efficient and simple chemical reaction, a method for synthesizing 6H-benzo[C]benzopyran compounds through a one-pot method in a relatively mild reaction system. Background technique [0002] Starting from simple compounds, the efficient synthesis of a series of compounds with complex molecular structures has become an important challenge in contemporary organic chemistry research. The reaction of the traditional simple catalytic system can no longer meet the requirements of environmental protection, energy saving and high efficiency in the field of contemporary chemistry. In recent years, the one-pot study of multiple catalytic reactions, such as tandem reactions, sequential catalytic reactions, etc., has attracted more and more attention. Because this type of reaction does not require the treatment and purification of the intermediates produced by the reaction, the target compound can be synthesized more efficiently (Adv. ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D311/80C07D491/052C07D495/04C07D209/08C07D209/10
CPCC07D209/08C07D209/10C07D311/80C07D491/052C07D495/04
Inventor 莫寒劼杨健国陈帝陈定奔潘诚敏
Owner TAIZHOU UNIV