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

The Journal of Organic Chemistry

Deacylation of pyrrole and other aromatic ketones

MW Moon, RA Wade

Index: Moon, M. W.; Wade, R. A. Journal of Organic Chemistry, 1984 , vol. 49, # 15 p. 2663 - 2669

Full Text: HTML

Citation Number: 8

Abstract

Discussion Reaction of formylpyrroles with glycols to give acetal derivatives has been reported by several group^?^ Acetals formed by using ethylene glycol are usually unstable and readily revert to the formylpyrrole on chromatography or~ rystallization.~~~ Stability of the acetals is increased when electron-withdrawing substituents are present in the pyrrole ring3?'or when ethylene glycol is replaced with a more hindered diol (2-methylpentane-2, ...

Ethanone, 1-(4-ethyl-3,5-dimethyl-1H-pyrrol-2-yl)- (9CI) Structure

Ethanone, 1-(4-...

~36%

2,4-Dimethyl-3-ethyl-1H-pyrrole Structure

2,4-Dimethyl-3-...

glycol monoacetate Structure

glycol monoacetate

4-benzoyl-3,5-dimethyl-1H-pyrrole-2-carboxylic acid ethyl ester Structure

4-benzoyl-3,5-d...

~0%

Ethyl 3,5-dimethyl-1H-pyrrole-2-carboxylate Structure

Ethyl 3,5-dimet...

2-(Benzoyloxy)ethanol Structure

2-(Benzoyloxy)e...

Ethanol, 2-[2- (benzoyloxy)ethoxy]- Structure

Ethanol, 2-[2- ...

Detail

1,2,5-trimethyl-3,4-diacetylpyrrole Structure

1,2,5-trimethyl...

~69%

1,2,5-TRIMETHYLPYRROLE Structure

1,2,5-TRIMETHYL...

4-acetyl-5-methyl-1-phenylpyrazole Structure

4-acetyl-5-meth...

~0%

5-METHYL-1-PHENYL-1H-PYRAZOLE Structure

5-METHYL-1-PHEN...

2-hydroxyethyl 4-methylbenzenesulfonate Structure

2-hydroxyethyl ...

acetic acid,ethane-1,2-diol,4-methylbenzenesulfonic acid Structure

acetic acid,eth...

Detail

4-acetyl-5-methyl-1-phenylpyrazole Structure

4-acetyl-5-meth...

Ethylene glycol Structure

Ethylene glycol

~0%

5-METHYL-1-PHENYL-1H-PYRAZOLE Structure

5-METHYL-1-PHEN...

2-hydroxyethyl 4-methylbenzenesulfonate Structure

2-hydroxyethyl ...

Detail

glycol monoacetate Structure

glycol monoacetate

p-Toluenesulfonic acid monohydrate Structure

p-Toluenesulfon...

Ethylene glycol Structure

Ethylene glycol

~0%

2-hydroxyethyl 4-methylbenzenesulfonate Structure

2-hydroxyethyl ...

Detail

3-acetyl-2,4-dimethyl-5-carbethoxypyrrole Structure

3-acetyl-2,4-di...

~99%

Ethyl 3,5-dimethyl-1H-pyrrole-2-carboxylate Structure

Ethyl 3,5-dimet...

N/A Structure

~57%

Ethyl 3,5-dimethyl-1H-pyrrole-2-carboxylate Structure

Ethyl 3,5-dimet...

4-benzoyl-3,5-dimethyl-1H-pyrrole-2-carboxylic acid ethyl ester Structure

4-benzoyl-3,5-d...

~97%

Ethyl 3,5-dimethyl-1H-pyrrole-2-carboxylate Structure

Ethyl 3,5-dimet...

2-(Benzoyloxy)ethanol Structure

2-(Benzoyloxy)e...

Ethanol, 2-[2- (benzoyloxy)ethoxy]- Structure

Ethanol, 2-[2- ...

Detail

4-benzoyl-3,5-dimethyl-1H-pyrrole-2-carboxylic acid ethyl ester Structure

4-benzoyl-3,5-d...

~51%

Ethyl 3,5-dimethyl-1H-pyrrole-2-carboxylate Structure

Ethyl 3,5-dimet...

1H-Pyrrole-3-carboxylicacid,5-acetyl-2,4-dimethyl-,methylester(9CI) Structure

1H-Pyrrole-3-ca...

~79%

1H-Pyrrole-3-carboxylicacid,2,4-dimethyl-,methylester(9CI) Structure

1H-Pyrrole-3-ca...

1H-Pyrrole-3-carboxylicacid,5-acetyl-2,4-dimethyl-,methylester(9CI) Structure

1H-Pyrrole-3-ca...

~0%

1H-Pyrrole-3-carboxylicacid,2,4-dimethyl-,methylester(9CI) Structure

1H-Pyrrole-3-ca...

4-benzoyl-3,5-dimethyl-1H-pyrrole-2-carboxylic acid ethyl ester Structure

4-benzoyl-3,5-d...

methyl 5-(2-methyl-1,3-dithiolan-2-yl)-1,2,4-trimethyl-1H-pyrrole-3-carboxylate Structure

methyl 5-(2-met...

~0%

1H-Pyrrole-3-carboxylicacid,2,4-dimethyl-,methylester(9CI) Structure

1H-Pyrrole-3-ca...

N/A Structure

1,2,4-trimethyl-pyrrole-3-carboxylic acid methyl ester Structure

1,2,4-trimethyl...

2-methyl-1,3-dithiolan-2-yl perchlorate Structure

2-methyl-1,3-di...

~0%

1H-Pyrrole-3-carboxylicacid,2,4-dimethyl-,methylester(9CI) Structure

1H-Pyrrole-3-ca...

N/A Structure

N/A Structure

~%

1H-Pyrrole-3-carboxylicacid,2,4-dimethyl-,methylester(9CI) Structure

1H-Pyrrole-3-ca...

1H-Pyrrole-3-carboxylicacid,5-acetyl-2,4-dimethyl-,methylester(9CI) Structure

1H-Pyrrole-3-ca...

1,2-Ethanedithiol Structure

1,2-Ethanedithiol

~0%

1H-Pyrrole-3-carboxylicacid,2,4-dimethyl-,methylester(9CI) Structure

1H-Pyrrole-3-ca...

N/A Structure

Hexylene glycol Structure

Hexylene glycol

1H-Pyrrole-3-carboxylicacid,5-acetyl-2,4-dimethyl-,methylester(9CI) Structure

1H-Pyrrole-3-ca...

~0%

1H-Pyrrole-3-carboxylicacid,2,4-dimethyl-,methylester(9CI) Structure

1H-Pyrrole-3-ca...

N/A Structure

Hexylene glycol Structure

Hexylene glycol

1H-Pyrrole-3-carboxylicacid,5-acetyl-2,4-dimethyl-,methylester(9CI) Structure

1H-Pyrrole-3-ca...

~%

1H-Pyrrole-3-carboxylicacid,2,4-dimethyl-,methylester(9CI) Structure

1H-Pyrrole-3-ca...

1H-Pyrrole-3-carboxylicacid,5-acetyl-2,4-dimethyl-,methylester(9CI) Structure

1H-Pyrrole-3-ca...

Ethylene glycol Structure

Ethylene glycol

~%

1H-Pyrrole-3-carboxylicacid,2,4-dimethyl-,methylester(9CI) Structure

1H-Pyrrole-3-ca...

1H-Pyrrole-3-carboxylicacid,5-acetyl-2,4-dimethyl-,methylester(9CI) Structure

1H-Pyrrole-3-ca...

1,2-Ethanedithiol Structure

1,2-Ethanedithiol

~%

1H-Pyrrole-3-carboxylicacid,2,4-dimethyl-,methylester(9CI) Structure

1H-Pyrrole-3-ca...

Ethanone, 1-(4-ethyl-3,5-dimethyl-1H-pyrrol-2-yl)- (9CI) Structure

Ethanone, 1-(4-...

~0%

2,4-Dimethyl-3-ethyl-1H-pyrrole Structure

2,4-Dimethyl-3-...

glycol monoacetate Structure

glycol monoacetate

4-acetyl-5-methyl-1-phenylpyrazole Structure

4-acetyl-5-meth...

~0%

5-METHYL-1-PHENYL-1H-PYRAZOLE Structure

5-METHYL-1-PHEN...

2-hydroxyethyl 4-methylbenzenesulfonate Structure

2-hydroxyethyl ...

acetic acid,ethane-1,2-diol,4-methylbenzenesulfonic acid Structure

acetic acid,eth...

Detail

4-acetyl-5-methyl-1-phenylpyrazole Structure

4-acetyl-5-meth...

Ethylene glycol Structure

Ethylene glycol

~0%

5-METHYL-1-PHENYL-1H-PYRAZOLE Structure

5-METHYL-1-PHEN...

2-hydroxyethyl 4-methylbenzenesulfonate Structure

2-hydroxyethyl ...

Detail

glycol monoacetate Structure

glycol monoacetate

p-Toluenesulfonic acid monohydrate Structure

p-Toluenesulfon...

Ethylene glycol Structure

Ethylene glycol

~79%

2-hydroxyethyl 4-methylbenzenesulfonate Structure

2-hydroxyethyl ...

Detail

3-Acetyl-2,4-dimethylpyrrole Structure

3-Acetyl-2,4-di...

~0%

2,4-Dimethylpyrrole Structure

2,4-Dimethylpyrrole

1,2-Ethanediol,1-formate Structure

1,2-Ethanediol,...

4-benzoyl-3,5-dimethyl-1H-pyrrole-2-carboxylic acid ethyl ester Structure

4-benzoyl-3,5-d...

~0%

Ethyl 3,5-dimethyl-1H-pyrrole-2-carboxylate Structure

Ethyl 3,5-dimet...

2-(Benzoyloxy)ethanol Structure

2-(Benzoyloxy)e...

Ethanol, 2-[2- (benzoyloxy)ethoxy]- Structure

Ethanol, 2-[2- ...

Detail

ethyl 5-acetyl-3,4-dimethyl-1H-pyrrole-2-carboxylate Structure

ethyl 5-acetyl-...

~90%

Ethyl 3,4-dimethyl-1H-pyrrole-2-carboxylate Structure

Ethyl 3,4-dimet...

4-benzoyl-3,5-dimethyl-1H-pyrrole-2-carboxylic acid ethyl ester Structure

4-benzoyl-3,5-d...

~0%

Ethyl 3,5-dimethyl-1H-pyrrole-2-carboxylate Structure

Ethyl 3,5-dimet...

2-(Benzoyloxy)ethanol Structure

2-(Benzoyloxy)e...

Ethanol, 2-[2- (benzoyloxy)ethoxy]- Structure

Ethanol, 2-[2- ...

Detail

Syntheses of per-15 N labeled etioporphyrins I–IV and a rela...

[Lash, Timothy D.; Chen, Shaohua Tetrahedron, 2005 , vol. 61, # 49 p. 11577 - 11600]

Structural analysis of tetrapyrroles by hydrogen chemical io...

[Shaw, George J.; Eglinton, Geoffrey; Quirke, J. Martin E. Analytical Chemistry, 1981 , vol. 53, # 13 p. 2014 - 2020]

Structural analysis of tetrapyrroles by hydrogen chemical io...

[Shaw, George J.; Eglinton, Geoffrey; Quirke, J. Martin E. Analytical Chemistry, 1981 , vol. 53, # 13 p. 2014 - 2020]

Structural analysis of tetrapyrroles by hydrogen chemical io...

[Shaw, George J.; Eglinton, Geoffrey; Quirke, J. Martin E. Analytical Chemistry, 1981 , vol. 53, # 13 p. 2014 - 2020]

Structural analysis of tetrapyrroles by hydrogen chemical io...

[Shaw, George J.; Eglinton, Geoffrey; Quirke, J. Martin E. Analytical Chemistry, 1981 , vol. 53, # 13 p. 2014 - 2020]