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

Formation of Acridones by Ethylene Extrusion in the Reaction of Arynes with β-Lactams and Dihydroquinolinones

Y Fang, DC Rogness, RC Larock…

Index: Fang, Yuesi; Rogness, Donald C.; Larock, Richard C.; Shi, Feng Journal of Organic Chemistry, 2012 , vol. 77, # 14 p. 6262 - 6270

Full Text: HTML

Citation Number: 27

Abstract

N-Unsubstituted β-lactams react with a molecule of aryne by insertion into the amide bond to form a 2, 3-dihydroquinolin-4-one, which subsequently reacts with another molecule of aryne to form an acridone by extrusion of a molecule of ethylene. 2, 3-Dihydroquinolin-4- ones react under the same reaction conditions to afford identical results. This is the first example of ethylene extrusion in aryne chemistry.

6-CHLORO-2,3-DIHYDROQUINOLIN-4(1H)-ONE Structure

6-CHLORO-2,3-DI...

2-trimethylsilylphenyl triflate Structure

2-trimethylsily...

~80%

9(10H)-Acridinone, 2-chloro-10-phenyl- Structure

9(10H)-Acridino...

N-(4'-chlorophenyl)-2-azetidinone Structure

N-(4'-chlorophe...

~%

9(10H)-Acridinone, 2-chloro-10-phenyl- Structure

9(10H)-Acridino...

3-bromo-N-(4-chlorophenyl)propanamide Structure

3-bromo-N-(4-ch...

~%

9(10H)-Acridinone, 2-chloro-10-phenyl- Structure

9(10H)-Acridino...

4-Chloroaniline Structure

4-Chloroaniline

~%

9(10H)-Acridinone, 2-chloro-10-phenyl- Structure

9(10H)-Acridino...

azetidinone Structure

2-trimethylsilylphenyl triflate Structure

2-trimethylsily...

~%

1-Phenyl-2-azetidinone Structure

1-Phenyl-2-azet...

1-Phenyl-2,3-dihydro-1H-quinolin-4-one Structure

1-Phenyl-2,3-di...

Detail

6-CHLORO-2,3-DIHYDROQUINOLIN-4(1H)-ONE Structure

6-CHLORO-2,3-DI...

methyl iodide Structure

~41%

6-chloro-1-methyl-2,3-dihydroquinolin-4-one Structure

6-chloro-1-meth...

N-(4'-chlorophenyl)-2-azetidinone Structure

N-(4'-chlorophe...

~%

6-chloro-1-methyl-2,3-dihydroquinolin-4-one Structure

6-chloro-1-meth...

3-bromo-N-(4-chlorophenyl)propanamide Structure

3-bromo-N-(4-ch...

~%

6-chloro-1-methyl-2,3-dihydroquinolin-4-one Structure

6-chloro-1-meth...

4-Chloroaniline Structure

4-Chloroaniline

~%

6-chloro-1-methyl-2,3-dihydroquinolin-4-one Structure

6-chloro-1-meth...

1-methyl-1,2,3,4-tetrahydroquinolin-4-one Structure

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

2-trimethylsilylphenyl triflate Structure

2-trimethylsily...

~61%

9(10H)-Acridinone,10-methyl- Structure

9(10H)-Acridino...

3-Methyl-2-oxazolidone Structure

3-Methyl-2-oxaz...

2-trimethylsilylphenyl triflate Structure

2-trimethylsily...

~32%

9(10H)-Acridinone,10-methyl- Structure

9(10H)-Acridino...

3-bromo-N-(4-methylphenyl)propanamide Structure

3-bromo-N-(4-me...

~%

6-METHYL-2,3-DIHYDROQUINOLIN-4(1H)-ONE Structure

6-METHYL-2,3-DI...

3-bromo-N-(4-chlorophenyl)propanamide Structure

3-bromo-N-(4-ch...

~%

6-CHLORO-2,3-DIHYDROQUINOLIN-4(1H)-ONE Structure

6-CHLORO-2,3-DI...

N-(4-methylphenyl)azetidin-2-one Structure

N-(4-methylphen...

~%

1,6-Dimethyl-2,3-dihydroquinolin-4(1H)-one Structure

1,6-Dimethyl-2,...

3-bromo-N-(4-methylphenyl)propanamide Structure

3-bromo-N-(4-me...

~%

1,6-Dimethyl-2,3-dihydroquinolin-4(1H)-one Structure

1,6-Dimethyl-2,...

p-Toluidine Structure

~%

1,6-Dimethyl-2,3-dihydroquinolin-4(1H)-one Structure

1,6-Dimethyl-2,...

2,3-Dihydro-1H-quinolin-4-one Structure

2,3-Dihydro-1H-...

2-trimethylsilylphenyl triflate Structure

2-trimethylsily...

~76%

10-phenylacridin-9-one Structure

10-phenylacridi...

azetidinone Structure

2-trimethylsilylphenyl triflate Structure

2-trimethylsily...

~49%

10-phenylacridin-9-one Structure

10-phenylacridi...

2,3-Dihydro-1H-quinolin-4-one Structure

2,3-Dihydro-1H-...

~%

10-phenylacridin-9-one Structure

10-phenylacridi...

1,2-Dibromoethane Structure

1,2-Dibromoethane

azetidinone Structure

2-trimethylsilylphenyl triflate Structure

2-trimethylsily...

~%

1-Phenyl-2-azetidinone Structure

1-Phenyl-2-azet...

1-Phenyl-2,3-dihydro-1H-quinolin-4-one Structure

1-Phenyl-2,3-di...

Detail

6-METHYL-2,3-DIHYDROQUINOLIN-4(1H)-ONE Structure

6-METHYL-2,3-DI...

methyl iodide Structure

~45%

1,6-Dimethyl-2,3-dihydroquinolin-4(1H)-one Structure

1,6-Dimethyl-2,...

2,3-Dihydro-1H-quinolin-4-one Structure

2,3-Dihydro-1H-...

~%

N/A Structure

3-methoxy-10-methylacridin-9-one Structure

3-methoxy-10-me...