e.g. Filippa Pettersson or Cancer Res. 75(6) , 1102-12, (2015) or 10.1002/anie.201600521

Transition??Metal??Free Intramolecular Ullmann??Type O??Arylation: Synthesis of Chromone Derivatives

J Zhao, Y Zhao, H Fu

Index: Zhao, Jie; Zhao, Yufen; Fu, Hua Angewandte Chemie - International Edition, 2011 , vol. 50, # 16 p. 3769 - 3773

Full Text: HTML

Citation Number: 61

Abstract

Aromatic CÀO bond-forming reactions are important in organic synthesis because these bonds occur in numerous natural products, biological compounds, pharmaceuticals, fragrances, cosmetics, and polymers.[1] Traditionally, aryl ethers have been prepared by copper-mediated Ullmann coupling reactions of aryl bromides/iodides and phenols, but the drawbacks include harsh reaction conditions, such as: the need for a strong base, long ...

1-(2-bromo-5-chlorophenyl)-3-(p-tolyl)propane-1,3-dione Structure

1-(2-bromo-5-ch...

~90%

6-chloro-2-(4-methylphenyl)chromen-4-one Structure

6-chloro-2-(4-m...

Methyl 2-bromo-5-chlorobenzoate Structure

Methyl 2-bromo-...

4'-Methylacetophenone Structure

4'-Methylacetop...

~%

6-chloro-2-(4-methylphenyl)chromen-4-one Structure

6-chloro-2-(4-m...

N/A Structure

~78%

4',6-DICHLOROFLAVONE Structure

4',6-DICHLOROFLAVONE

Methyl 2-bromo-5-chlorobenzoate Structure

Methyl 2-bromo-...

1-(4-Chlorophenyl)ethanone Structure

1-(4-Chlorophen...

~%

4',6-DICHLOROFLAVONE Structure

4',6-DICHLOROFLAVONE

1-(2-bromo-5-chlorophenyl)-3-phenylpropane-1,3-dione Structure

1-(2-bromo-5-ch...

~99%

4H-1-Benzopyran-4-one,6-chloro-2-phenyl- Structure

4H-1-Benzopyran...

1-(2-bromo-5-chlorophenyl)butane-1,3-dione Structure

1-(2-bromo-5-ch...

~72%

6-CHLORO-2-METHYL-4H-CHROMEN-4-ONE Structure

6-CHLORO-2-METH...

Methyl 2-bromo-5-chlorobenzoate Structure

Methyl 2-bromo-...

~%

6-CHLORO-2-METHYL-4H-CHROMEN-4-ONE Structure

6-CHLORO-2-METH...

N/A Structure

~83%

6-Methylflavone Structure

6-Methylflavone

Acetophenone Structure

methyl 2-bromo-5-methylbenzoate Structure

methyl 2-bromo-...

~%

6-Methylflavone Structure

6-Methylflavone

1-(2-BROMO-PHENYL)-BUTANE-1,3-DIONE Structure

1-(2-BROMO-PHEN...

~81%

2-Methylchromone Structure

2-Methylchromone

Methyl 2-bromobenzoate Structure

Methyl 2-bromob...

~%

2-Methylchromone Structure

2-Methylchromone

Methyl 2-bromobenzoate Structure

Methyl 2-bromob...

Acetone Structure

~%

1-(2-BROMO-PHENYL)-BUTANE-1,3-DIONE Structure

1-(2-BROMO-PHEN...

N/A Structure

~96%

4'-Methoxyflavone Structure

4'-Methoxyflavone

2-[2-Chlor-phenyl]-4-[4-methoxy-phenyl]-dioxol-(1,3) Structure

2-[2-Chlor-phen...

~86%

4'-Methoxyflavone Structure

4'-Methoxyflavone

Methyl 2-chlorobenzoate Structure

Methyl 2-chloro...

Acetanisole Structure

~%

4'-Methoxyflavone Structure

4'-Methoxyflavone

Methyl 2-bromobenzoate Structure

Methyl 2-bromob...

Acetanisole Structure

~%

4'-Methoxyflavone Structure

4'-Methoxyflavone

Methyl 2-chlorobenzoate Structure

Methyl 2-chloro...

1-(4-Chlorophenyl)ethanone Structure

1-(4-Chlorophen...

~%

4H-1-BENZOPYRAN-4-ONE, 2-(4-CHLOROPHENYL)- Structure

4H-1-BENZOPYRAN...

Methyl 2-bromobenzoate Structure

Methyl 2-bromob...

1-(4-Chlorophenyl)ethanone Structure

1-(4-Chlorophen...

~%

4H-1-BENZOPYRAN-4-ONE, 2-(4-CHLOROPHENYL)- Structure

4H-1-BENZOPYRAN...

1-(2-bromo-5-chlorophenyl)-3-(4-methoxyphenyl)propane-1,3-dione Structure

1-(2-bromo-5-ch...

~95%

6-chloro-2-(4-methoxyphenyl)chromen-4-one Structure

6-chloro-2-(4-m...

Methyl 2-bromo-5-chlorobenzoate Structure

Methyl 2-bromo-...

Acetanisole Structure

~%

6-chloro-2-(4-methoxyphenyl)chromen-4-one Structure

6-chloro-2-(4-m...

1-(2-bromophenyl)-3-p-tolylpropane-1,3-dione Structure

1-(2-bromopheny...

~96%

4H-1-BENZOPYRAN-4-ONE, 2-(4-METHYLPHENYL)- Structure

4H-1-BENZOPYRAN...

Methyl 2-chlorobenzoate Structure

Methyl 2-chloro...

4'-Methylacetophenone Structure

4'-Methylacetop...

~%

4H-1-BENZOPYRAN-4-ONE, 2-(4-METHYLPHENYL)- Structure

4H-1-BENZOPYRAN...

Methyl 2-bromobenzoate Structure

Methyl 2-bromob...

4'-Methylacetophenone Structure

4'-Methylacetop...

~%

4H-1-BENZOPYRAN-4-ONE, 2-(4-METHYLPHENYL)- Structure

4H-1-BENZOPYRAN...

K2CO3-Catalyzed Synthesis of Chromones and 4-Quinolones thro...

[Zhao, Jie; Zhao, Yufen; Fu, Hua Organic Letters, 2012 , vol. 14, # 11 p. 2710 - 2713]