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

A modular synthesis of unsymmetrical tetraarylazadipyrromethenes

…, SO McDonnell, J Killoran, DF O'Shea

Index: Hall, Michael J.; McDonnell, Shane O.; Killoran, John; O'Shea, Donal F. Journal of Organic Chemistry, 2005 , vol. 70, # 14 p. 5571 - 5578

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Citation Number: 83

Abstract

A stepwise route to unsymmetrical tetraarylazadipyrromethenes by a condensation of 2, 4- diaryl-5-nitroso-pyrroles with 2, 4-diarylpyrroles is described. This modular building-block approach allows for the introduction of up to four different aryl substituents on the azadipyrromethene and is tolerant of a varied substituent set. An efficient synthesis of the 2, 4-diarylpyrroles building blocks from 1, 3-diaryl-4-nitro-butan-1-ones by nitro hydrolysis to ...

(E)-1-(4-BROMOPHENYL)-3-PHENYLPROPENONE Structure

(E)-1-(4-BROMOP...

~%

4-(P-BROMOPHENYL)-2-PHENYLPYRROLE Structure

4-(P-BROMOPHENY...

4-Bromobenzaldehyde Structure

4-Bromobenzaldehyde

~%

4-(P-BROMOPHENYL)-2-PHENYLPYRROLE Structure

4-(P-BROMOPHENY...

Acetophenone Structure

~%

4-(P-BROMOPHENYL)-2-PHENYLPYRROLE Structure

4-(P-BROMOPHENY...

3-(4-bromophenyl)-4-nitro-1-phenylbutan-1-one Structure

3-(4-bromopheny...

~%

4-(P-BROMOPHENYL)-2-PHENYLPYRROLE Structure

4-(P-BROMOPHENY...

1-(4-fluorophenyl)-4-nitro-3-phenyl-butan-1-one Structure

1-(4-fluorophen...

~%

2-(P-FLUOROPHENYL)-4-PHENYLPYRROLE Structure

2-(P-FLUOROPHEN...

(E)-1-(4-Fluorophenyl)-3-phenylprop-2-en-1-one Structure

(E)-1-(4-Fluoro...

~%

2-(P-FLUOROPHENYL)-4-PHENYLPYRROLE Structure

2-(P-FLUOROPHEN...

4'-Fluoroacetophenone Structure

4'-Fluoroacetop...

~%

2-(P-FLUOROPHENYL)-4-PHENYLPYRROLE Structure

2-(P-FLUOROPHEN...

Benzaldehyde Structure

~%

2-(P-FLUOROPHENYL)-4-PHENYLPYRROLE Structure

2-(P-FLUOROPHEN...

3-(4-dimethylaminophenyl)-4-nitro-1-phenyl-butan-1-one Structure

3-(4-dimethylam...

~%

2-PHENYL-4-(P-DIMETHYLAMINOPHENYL)-PYRROLE Structure

2-PHENYL-4-(P-D...

Acetophenone Structure

~%

2-PHENYL-4-(P-DIMETHYLAMINOPHENYL)-PYRROLE Structure

2-PHENYL-4-(P-D...

p-Dimethylaminobenzaldehyde Structure

p-Dimethylamino...

~%

2-PHENYL-4-(P-DIMETHYLAMINOPHENYL)-PYRROLE Structure

2-PHENYL-4-(P-D...

1H-Pyrrole,2,4-diphenyl- Structure

1H-Pyrrole,2,4-...

~76%

2-nitroso-3,5-diphenyl-1H-pyrrole Structure

2-nitroso-3,5-d...

4,4-dimethoxy-1,3-diphenyl-butan-1-one Structure

4,4-dimethoxy-1...

~%

2-nitroso-3,5-diphenyl-1H-pyrrole Structure

2-nitroso-3,5-d...

1-Butanone,4-nitro-1,3-diphenyl- Structure

1-Butanone,4-ni...

~%

2-nitroso-3,5-diphenyl-1H-pyrrole Structure

2-nitroso-3,5-d...

3-(diethylaminomethyl-phenyl)-4-nitro-1-phenyl-butan-1-one Structure

3-(diethylamino...

~%

N-ethyl-N-[[4-(5-phenyl-1H-pyrrol-3-yl)phenyl]methyl]ethanamine Structure

N-ethyl-N-[[4-(...

p-Dimethylaminobenzaldehyde Structure

p-Dimethylamino...

~%

N-ethyl-N-[[4-(5-phenyl-1H-pyrrol-3-yl)phenyl]methyl]ethanamine Structure

N-ethyl-N-[[4-(...

4'-Methoxychalcone Structure

4'-Methoxychalcone

~%

2-(4-methoxyphenyl)-4-phenyl-1H-pyrrole Structure

2-(4-methoxyphe...

1-(4-methoxyphenyl)-4-nitro-3-phenylbutan-1-one Structure

1-(4-methoxyphe...

~%

2-(4-methoxyphenyl)-4-phenyl-1H-pyrrole Structure

2-(4-methoxyphe...

4-Methoxychalcone Structure

4-Methoxychalcone

~%

4-(P-METHOXYPHENYL)-2-PHENYLPYRROLE Structure

4-(P-METHOXYPHE...

3-(4-methoxyphenyl)-4-nitro-1-phenylbutan-1-one Structure

3-(4-methoxyphe...

~%

4-(P-METHOXYPHENYL)-2-PHENYLPYRROLE Structure

4-(P-METHOXYPHE...

morpholine Structure

4-Bromomethylbenzaldehyde Structure

4-Bromomethylbe...

~85%

4-(MORPHOLINOMETHYL)BENZALDEHYDE Structure

4-(MORPHOLINOME...

4,4-dimethoxy-1,3-diphenyl-butan-1-one Structure

4,4-dimethoxy-1...

~%

1H-Pyrrole,2,4-diphenyl- Structure

1H-Pyrrole,2,4-...