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

The Journal of Organic Chemistry

Quinone chemistry. Reaction of 2, 3-dichloro-1, 4-naphthoquinone with arylamines in pyridine

NL Agarwal, W Schaefer

Index: Agarwal, Nand L.; Schaefer, Wolfram Journal of Organic Chemistry, 1980 , vol. 45, # 25 p. 5139 - 5143

Full Text: HTML

Citation Number: 20

Abstract

2, 3-Dichloro-1, 4-naphthoquinone (1) reacts with arylamines (2) in pyridine to afford 2- (arylamino)-3-chloro-1, 4-naphthoquinone (6), 2-(arylamino)-1, 4-naphthoquinone (5), 2- (arylamino)-1, 4-naphthoquinone-3-pyridinium perchlorate (4), and 2-amino-1, 4- naphthoquinone-3-pyridinium perchlorate (7), depending upon the nature of the substituent in 2. 2-(4-Nitroanilino)-l, 4-naphthoquinone-3-pyridinium chloride (4e, X= C1) reacts with ...

2,3-Dichlor-1,4-naphthochinone Structure

2,3-Dichlor-1,4...

4-Chloroaniline Structure

4-Chloroaniline

~%

1,4-Naphthalenedione,2-[(4-chlorophenyl)amino]- Structure

1,4-Naphthalene...

1,4-Naphthalenedione,2-chloro-3-[(4-chlorophenyl)amino]- Structure

1,4-Naphthalene...

Detail

2,3-Dichlor-1,4-naphthochinone Structure

2,3-Dichlor-1,4...

p-Toluidine Structure

~%

2-chloro-3-[(4-methylphenyl)amino]naphthalene-1,4-dione Structure

2-chloro-3-[(4-...

2-[(4-methylphenyl)amino]naphthalene-1,4-dione Structure

2-[(4-methylphe...

Detail

Pyridine Structure

2,3-Dichlor-1,4-naphthochinone Structure

2,3-Dichlor-1,4...

p-Toluidine Structure

~%

2-chloro-3-[(4-methylphenyl)amino]naphthalene-1,4-dione Structure

2-chloro-3-[(4-...

Detail

Pyridine Structure

2,3-Dichlor-1,4-naphthochinone Structure

2,3-Dichlor-1,4...

4-Chloroaniline Structure

4-Chloroaniline

~%

1,4-Naphthalenedione,2-[(4-chlorophenyl)amino]- Structure

1,4-Naphthalene...

Detail

2,3-Dichlor-1,4-naphthochinone Structure

2,3-Dichlor-1,4...

p-Anisidine Structure

~%

1,4-Naphthalenedione,2-[(4-methoxyphenyl)amino]- Structure

1,4-Naphthalene...

2-chloro-3-(4-methoxyanilino)naphthalene-1,4-dione Structure

2-chloro-3-(4-m...

Detail

Pyridine Structure

2,3-Dichlor-1,4-naphthochinone Structure

2,3-Dichlor-1,4...

p-Anisidine Structure

~%

1,4-Naphthalenedione,2-[(4-methoxyphenyl)amino]- Structure

1,4-Naphthalene...

Detail

2,3-Dichlor-1,4-naphthochinone Structure

2,3-Dichlor-1,4...

p-Anisidine Structure

~%

1,4-Naphthalenedione,2-[(4-methoxyphenyl)amino]- Structure

1,4-Naphthalene...

2-chloro-3-(4-methoxyanilino)naphthalene-1,4-dione Structure

2-chloro-3-(4-m...

Detail

Pyridine Structure

2,3-Dichlor-1,4-naphthochinone Structure

2,3-Dichlor-1,4...

p-Anisidine Structure

~%

1,4-Naphthalenedione,2-[(4-methoxyphenyl)amino]- Structure

1,4-Naphthalene...

Detail

Pyridine Structure

2,3-Dichlor-1,4-naphthochinone Structure

2,3-Dichlor-1,4...

~%

2-[(4-nitrophenyl)amino]naphthalene-1,4-dione Structure

2-[(4-nitrophen...

2-amino-1,4-naphthoquinone-3-pyridinium perchlorate Structure

2-amino-1,4-nap...

2,3-Dichlor-1,4-naphthochinone Structure

2,3-Dichlor-1,4...

4-Nitroaniline Structure

~%

2-[(4-nitrophenyl)amino]naphthalene-1,4-dione Structure

2-[(4-nitrophen...

2-amino-1,4-naphthoquinone-3-pyridinium perchlorate Structure

2-amino-1,4-nap...

2-(4-chloroanilino)-1,4-naphthoquinone-3-pyridinium chloride Structure

2-(4-chloroanil...

~1%

1,4-Naphthalenedione,2-[(4-chlorophenyl)amino]- Structure

1,4-Naphthalene...

2,3-Dichlor-1,4-naphthochinone Structure

2,3-Dichlor-1,4...

~%

1,4-Naphthalenedione,2-[(4-chlorophenyl)amino]- Structure

1,4-Naphthalene...

4-Chloroaniline Structure

4-Chloroaniline

~%

1,4-Naphthalenedione,2-[(4-chlorophenyl)amino]- Structure

1,4-Naphthalene...

2,3-Dichlor-1,4-naphthochinone Structure

2,3-Dichlor-1,4...

4-Chloroaniline Structure

4-Chloroaniline

~%

1,4-Naphthalenedione,2-[(4-chlorophenyl)amino]- Structure

1,4-Naphthalene...

1,4-Naphthalenedione,2-chloro-3-[(4-chlorophenyl)amino]- Structure

1,4-Naphthalene...

Detail

Pyridine Structure

2,3-Dichlor-1,4-naphthochinone Structure

2,3-Dichlor-1,4...

4-Chloroaniline Structure

4-Chloroaniline

~%

1,4-Naphthalenedione,2-[(4-chlorophenyl)amino]- Structure

1,4-Naphthalene...

Detail

2-amino-1,4-naphthoquinone-3-pyridinium perchlorate Structure

2-amino-1,4-nap...

~91%

Pyridinium,1-(1,4-dihydro-3-hydroxy-1,4-dioxo-2-naphthalenyl)-, inner salt Structure

Pyridinium,1-(1...

2,3-Dichlor-1,4-naphthochinone Structure

2,3-Dichlor-1,4...

~%

Pyridinium,1-(1,4-dihydro-3-hydroxy-1,4-dioxo-2-naphthalenyl)-, inner salt Structure

Pyridinium,1-(1...

Pyridine Structure

~%

Pyridinium,1-(1,4-dihydro-3-hydroxy-1,4-dioxo-2-naphthalenyl)-, inner salt Structure

Pyridinium,1-(1...

2,3-Dichlor-1,4-naphthochinone Structure

2,3-Dichlor-1,4...

p-Toluidine Structure

~%

2-chloro-3-[(4-methylphenyl)amino]naphthalene-1,4-dione Structure

2-chloro-3-[(4-...

2-[(4-methylphenyl)amino]naphthalene-1,4-dione Structure

2-[(4-methylphe...

Detail

Pyridine Structure

2,3-Dichlor-1,4-naphthochinone Structure

2,3-Dichlor-1,4...

p-Toluidine Structure

~%

2-chloro-3-[(4-methylphenyl)amino]naphthalene-1,4-dione Structure

2-chloro-3-[(4-...

Detail

Spectroscopic and theoretical studies on the nucleophilic su...

[Satheshkumar, Angupillai; Elango, Kuppanagounder P. Spectrochimica Acta, Part A: Molecular and Biomolecular Spectroscopy, 2012 , vol. 98, p. 378 - 383,6]