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

Tetrahedron

A convenient approach to 1, 4-dihydro-4-oxo-3-quinoline carboxylates by electro-oxidative formation of enamine moiety

S Torii, H Okumoto, LH Xu

Index: Torii, Sigeni; Okumoto, Hiroshi; Xu, Long He Tetrahedron, 1991 , vol. 47, # 4-5 p. 665 - 674

Full Text: HTML

Citation Number: 2

Abstract

A practical synthetic approach to the drugs of current interest, 1, 4-dihydro-4-oxo-quinoline-3- carboxylic acids, has been accomplished through the electro-oxidative formation of double bond adjacent to the nitrogen atom. The efficiency was shown by the introduction of some representative substituents at the C7 position.

Pyrrolidine Structure

7-chloro-1-ethyl-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid Structure

7-chloro-1-ethy...

~86%

1-ethyl-4-oxo-7-pyrrolidin-1-ylquinoline-3-carboxylic acid Structure

1-ethyl-4-oxo-7...

methyl 4-chloro-2-((3-methoxy-3-oxopropyl)amino)benzoate Structure

methyl 4-chloro...

~%

1-ethyl-4-oxo-7-pyrrolidin-1-ylquinoline-3-carboxylic acid Structure

1-ethyl-4-oxo-7...

METHYL 7-CHLORO-4-OXO-1,4-DIHYDROQUINOLINE-3-CARBOXYLATE Structure

METHYL 7-CHLORO...

~%

1-ethyl-4-oxo-7-pyrrolidin-1-ylquinoline-3-carboxylic acid Structure

1-ethyl-4-oxo-7...

1-Acetyl-7-chloro-1,2-dihydro-4-hydroxy-quinoline-3-carboxylic acid methyl ester Structure

1-Acetyl-7-chlo...

~%

1-ethyl-4-oxo-7-pyrrolidin-1-ylquinoline-3-carboxylic acid Structure

1-ethyl-4-oxo-7...

1-Methoxycarbonyl-7-chloro-1,2-dihydro-4-hydroxy-quinoline-3-carboxylic acid methyl ester Structure

1-Methoxycarbon...

~%

1-ethyl-4-oxo-7-pyrrolidin-1-ylquinoline-3-carboxylic acid Structure

1-ethyl-4-oxo-7...

methyl 7-chloro-1-ethyl-4-oxo-1,4-dihydroquinoline-3-carboxylate Structure

methyl 7-chloro...

~%

1-ethyl-4-oxo-7-pyrrolidin-1-ylquinoline-3-carboxylic acid Structure

1-ethyl-4-oxo-7...

1-Methoxycarbonyl-1,2-dihydro-4-hydroxy-quinoline-3-carboxylic acid methyl ester Structure

1-Methoxycarbon...

~90%

Methyl 4-oxo-1,4-dihydroquinoline-3-carboxylate Structure

Methyl 4-oxo-1,...

Benzoic acid,2-[(3-methoxy-3-oxopropyl)amino]-, methyl ester Structure

Benzoic acid,2-...

~%

Methyl 4-oxo-1,4-dihydroquinoline-3-carboxylate Structure

Methyl 4-oxo-1,...

methyl 3-[N-acetyl-(o-methoxycarbonyl)anilino]propanoate Structure

methyl 3-[N-ace...

~%

Methyl 4-oxo-1,4-dihydroquinoline-3-carboxylate Structure

Methyl 4-oxo-1,...

methyl 2-((3-methoxy-3-oxopropyl)(methoxycarbonyl)amino)benzoate Structure

methyl 2-((3-me...

~%

Methyl 4-oxo-1,4-dihydroquinoline-3-carboxylate Structure

Methyl 4-oxo-1,...

N/A Structure

~67%

Methyl 4-oxo-1,4-dihydroquinoline-3-carboxylate Structure

Methyl 4-oxo-1,...

1-ethyl-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid methyl ester Structure

1-ethyl-4-oxo-1...

~92%

1-ethyl-4-oxo-1,4-dihydroquinoline-3-carboxylic acid(SALTDATA: FREE) Structure

1-ethyl-4-oxo-1...

1-Methoxycarbonyl-7-chloro-1,2-dihydro-4-hydroxy-quinoline-3-carboxylic acid methyl ester Structure

1-Methoxycarbon...

~85%

METHYL 7-CHLORO-4-OXO-1,4-DIHYDROQUINOLINE-3-CARBOXYLATE Structure

METHYL 7-CHLORO...

1-Acetyl-7-chloro-1,2-dihydro-4-hydroxy-quinoline-3-carboxylic acid methyl ester Structure

1-Acetyl-7-chlo...

~81%

METHYL 7-CHLORO-4-OXO-1,4-DIHYDROQUINOLINE-3-CARBOXYLATE Structure

METHYL 7-CHLORO...

methyl 4-chloro-2-((3-methoxy-3-oxopropyl)amino)benzoate Structure

methyl 4-chloro...

~%

METHYL 7-CHLORO-4-OXO-1,4-DIHYDROQUINOLINE-3-CARBOXYLATE Structure

METHYL 7-CHLORO...