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

The Journal of organic chemistry

Cascade Synthesis of 3-Quinolinecarboxylic Ester via Benzylation/Propargylation− Cyclization

J Fan, C Wan, G Sun, Z Wang

Index: Fan, Jinmin; Wan, Changfeng; Sun, Gaojun; Wang, Zhiyong Journal of Organic Chemistry, 2008 , vol. 73, # 21 p. 8608 - 8611

Full Text: HTML

Citation Number: 54

Abstract

Reactions of 2-amino-aryl alcohols with β-ketoesters catalyzed by a catalytic amout of FeCl3 via tandem benzylation− cyclization produce the corresponding 3-quinolinecarboxylic esters in good to high yields. Extending this methodology to propargylation− cyclization, 2- nitrophenyl propargyl alcohols with β-ketoesters catalyzed by FeCl3 and SnCl2 also produce the 4-alkyne-3-quinolinecarboxylic esters. The mechanistic details of this ...

Ethyl 3-oxohexanoate Structure

Ethyl 3-oxohexanoate

1-(2-nitrophenyl)-3-phenyl-2-propyn-1-ol Structure

1-(2-nitropheny...

~66%

ethyl 4-(2-phenylethynyl)-2-propyl-quinoline-3-carboxylate Structure

ethyl 4-(2-phen...

(4-methoxy-phenyl)-(2-nitro-phenyl)-methanol Structure

(4-methoxy-phen...

~%

(2-Aminophenyl)(4-methoxyphenyl)methanol Structure

(2-Aminophenyl)...

(2-Aminophenyl)(4-methoxyphenyl)methanol Structure

(2-Aminophenyl)...

Ethyl 2-oxobutanoate Structure

Ethyl 2-oxobutanoate

~94%

ethyl 4-(4-methoxyphenyl)-2-methyl-quinoline-3-carboxylate Structure

ethyl 4-(4-meth...

1-(2-nitrophenyl)-3-phenyl-2-propyn-1-ol Structure

1-(2-nitropheny...

~74%

2-Phenylquinoline Structure

2-Phenylquinoline

Ethyl 2-oxobutanoate Structure

Ethyl 2-oxobutanoate

rac-(2-amino-5-chloro-phenyl)-phenyl-methanol Structure

rac-(2-amino-5-...

~87%

6-Chloro-3-ethoxycarbonyl-2-methyl-4-phenylquinoline Structure

6-Chloro-3-etho...

Ethyl 2-oxobutanoate Structure

Ethyl 2-oxobutanoate

(2-aminophenyl)-(2-thienyl)methanol Structure

(2-aminophenyl)...

~84%

ethyl 2-methyl-4-(2-thienyl)quinoline-3-carboxylate Structure

ethyl 2-methyl-...

1-(5-chloro-2-nitro-phenyl)-3-phenyl-prop-2-yn-1-ol Structure

1-(5-chloro-2-n...

Ethyl 3-oxo-3-phenylpropanoate Structure

Ethyl 3-oxo-3-p...

~70%

ethyl 6-chloro-2-phenyl-4-(2-phenylethynyl)quinoline-3-carboxylat e Structure

ethyl 6-chloro-...

(2-Aminophenyl)methanol Structure

(2-Aminophenyl)...

Ethyl 2-oxobutanoate Structure

Ethyl 2-oxobutanoate

~65%

Ethyl 2-methyl-3-quinolinecarboxylate Structure

Ethyl 2-methyl-...

5-Chloro-2-nitrobenzaldehyde Structure

5-Chloro-2-nitr...

Phenylacetylene Structure

Phenylacetylene

~%

1-(5-chloro-2-nitro-phenyl)-3-phenyl-prop-2-yn-1-ol Structure

1-(5-chloro-2-n...

Benzenemethanol,2-amino-a-phenyl- Structure

Benzenemethanol...

Methyl Isobutyrylacetate Structure

Methyl Isobutyr...

~66%

methyl 2-isopropyl-4-phenyl-quinoline-3-carboxylate Structure

methyl 2-isopro...

Ethyl 2-oxobutanoate Structure

Ethyl 2-oxobutanoate

(2-aminophenyl)-(2-furyl)methanol Structure

(2-aminophenyl)...

~89%

ethyl 4-(2-furyl)-2-methyl-quinoline-3-carboxylate Structure

ethyl 4-(2-fury...

Benzenemethanol,2-amino-a-phenyl- Structure

Benzenemethanol...

Ethyl 3-oxo-3-phenylpropanoate Structure

Ethyl 3-oxo-3-p...

~84%

Ethyl 2,4-diphenyl-3-quinolinecarboxylate Structure

Ethyl 2,4-diphe...

Thiophene(SIV) Structure

2-Nitrobenzoyl chloride Structure

2-Nitrobenzoyl ...

~%

(2-nitrophenyl)-thiophen-2-yl-methanone Structure

(2-nitrophenyl)...

Ethyl 3-oxo-3-phenylpropanoate Structure

Ethyl 3-oxo-3-p...

rac-(2-amino-5-chloro-phenyl)-phenyl-methanol Structure

rac-(2-amino-5-...

~78%

Ethyl 6-chloro-2,4-diphenyl-3-quinolinecarboxylate Structure

Ethyl 6-chloro-...

Benzenemethanol,2-amino-a-phenyl- Structure

Benzenemethanol...

Ethyl 3-oxohexanoate Structure

Ethyl 3-oxohexanoate

~82%

ethyl 4-phenyl-2-propyl-quinoline-3-carboxylate Structure

ethyl 4-phenyl-...