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

A new synthetic route to 3-acylamino-1-aryl-2-pyrazolin-5-ones

CK Kim, PA Zielinski, CA Maggiulli

Index: Kim, Chang-Kyu; Zielinski, Paul A.; Maggiulli, Cataldo A. Journal of Organic Chemistry, 1984 , vol. 49, # 26 p. 5247 - 5250

Full Text: HTML

Citation Number: 18

Abstract

(7) Another CCN system where-C= C- is the part of benzene and thus the heterocycle formed is indazole was reported while our investi-gation was under way. See: Vivona, N.; Cusmano, G.; Macaluso, G.; Frenna, V.; Ruccia, MJ Heterocycl. Chem. 1979, 16, 783.(8) It is interesting to note that even the oxadiazole with a saturated CHzCHzNHR side chain instead of-C= CN- undergoes the rear-rangement reaction to give a nonaromatic ...

2-(5-methyl-1,2,4-oxadiazol-3-yl)-N-(2,4,6-trichlorophenyl)acetamide Structure

2-(5-methyl-1,2...

~57%

3-Propeneamido-1-(2,4,6-trichlorophenyl)-5-pyrazolone Structure

3-Propeneamido-...

2,4,6-Trichloroaniline Structure

2,4,6-Trichloro...

2-cyano-2',4',6'-trichloroacetanilide Structure

2-cyano-2',4',6...

~%

3-Propeneamido-1-(2,4,6-trichlorophenyl)-5-pyrazolone Structure

3-Propeneamido-...

(Z)-3-(acetoxyimino)-3-amino-N-(2,4,6-trichlorophenyl)propanamide Structure

(Z)-3-(acetoxyi...

~%

3-Propeneamido-1-(2,4,6-trichlorophenyl)-5-pyrazolone Structure

3-Propeneamido-...

3-Propeneamido-1-(2,4,6-trichlorophenyl)-5-pyrazolone Structure

3-Propeneamido-...

~78%

1-(2,4,6-Trichlorophenyl)-3-amino-pyrazolin-5-one Structure

1-(2,4,6-Trichl...

2-cyano-2',4',6'-trichloroacetanilide Structure

2-cyano-2',4',6...

~%

1-(2,4,6-Trichlorophenyl)-3-amino-pyrazolin-5-one Structure

1-(2,4,6-Trichl...

2-(5-methyl-1,2,4-oxadiazol-3-yl)-N-(2,4,6-trichlorophenyl)acetamide Structure

2-(5-methyl-1,2...

~%

1-(2,4,6-Trichlorophenyl)-3-amino-pyrazolin-5-one Structure

1-(2,4,6-Trichl...

(Z)-3-(acetoxyimino)-3-amino-N-(2,4,6-trichlorophenyl)propanamide Structure

(Z)-3-(acetoxyi...

~%

1-(2,4,6-Trichlorophenyl)-3-amino-pyrazolin-5-one Structure

1-(2,4,6-Trichl...

5-(4-Nitrophenoxymethyl)-3-[2-oxo-2-(2,4,6-trichloroanilino)ethyl]-1,2,4-oxadiazole Structure

5-(4-Nitropheno...

~75%

3H-Pyrazol-3-one,2,4-dihydro-5-[(4-nitrophenyl)amino]-2-(2,4,6-trichlorophenyl)- Structure

3H-Pyrazol-3-on...

O-(4-Nitrophenoxyacetyl)-3-oxo-3-(2,4,6-trichloroanilino)propionamidoxime Structure

O-(4-Nitropheno...

~%

3H-Pyrazol-3-one,2,4-dihydro-5-[(4-nitrophenyl)amino]-2-(2,4,6-trichlorophenyl)- Structure

3H-Pyrazol-3-on...

3-amino-3-(hydroxyimino)-N-(2,4,6-trichlorophenyl)propanamide Structure

3-amino-3-(hydr...

~%

3H-Pyrazol-3-one,2,4-dihydro-5-[(4-nitrophenyl)amino]-2-(2,4,6-trichlorophenyl)- Structure

3H-Pyrazol-3-on...

2-(4-nitrophenoxy)acetyl chloride Structure

2-(4-nitropheno...

~%

3H-Pyrazol-3-one,2,4-dihydro-5-[(4-nitrophenyl)amino]-2-(2,4,6-trichlorophenyl)- Structure

3H-Pyrazol-3-on...

5-(4-Nitrophenoxymethyl)-3-[2-oxo-2-(2,4,6-trichloroanilino)ethyl]-1,2,4-oxadiazole Structure

5-(4-Nitropheno...

~%

N/A Structure

3H-Pyrazol-3-one,2,4-dihydro-5-[(4-nitrophenyl)amino]-2-(2,4,6-trichlorophenyl)- Structure

3H-Pyrazol-3-on...

5-Methyl-3-(2-oxo-2-anilinoethyl)-1,2,4-oxadiazole Structure

5-Methyl-3-(2-o...

~41%

N-(5-oxo-1-phenyl-4H-pyrazol-3-yl)acetamide Structure

N-(5-oxo-1-phen...

2-Cyano-N-phenylacetamide Structure

2-Cyano-N-pheny...

~%

N-(5-oxo-1-phenyl-4H-pyrazol-3-yl)acetamide Structure

N-(5-oxo-1-phen...

3-amino-3-hydroxyimino-N-phenylpropanamide Structure

3-amino-3-hydro...

~%

N-(5-oxo-1-phenyl-4H-pyrazol-3-yl)acetamide Structure

N-(5-oxo-1-phen...

(Z)-3-(acetoxyimino)-3-amino-N-(2,4,6-trichlorophenyl)propanamide Structure

(Z)-3-(acetoxyi...

~95%

2-(5-methyl-1,2,4-oxadiazol-3-yl)-N-(2,4,6-trichlorophenyl)acetamide Structure

2-(5-methyl-1,2...

2-cyano-2',4',6'-trichloroacetanilide Structure

2-cyano-2',4',6...

~%

2-(5-methyl-1,2,4-oxadiazol-3-yl)-N-(2,4,6-trichlorophenyl)acetamide Structure

2-(5-methyl-1,2...

N-(5-oxo-1-phenyl-4H-pyrazol-3-yl)acetamide Structure

N-(5-oxo-1-phen...

~73%

3H-Pyrazol-3-one,5-amino-2,4-dihydro-2-phenyl- Structure

3H-Pyrazol-3-on...