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

Journal of heterocyclic chemistry

Indole esters as heterocyclic synthons. III. Preparation and reactions of furo [3, 2??b] indoles

PC Unangst, ME Carethers

Index: Unangst, Paul C.; Carethers, Mary E. Journal of Heterocyclic Chemistry, 1984 , vol. 21, p. 709 - 714

Full Text: HTML

Citation Number: 8

Abstract

Abstract The preparation of furo [3, 2-b] indoles via Dieckmann cyclization is described. The precursor diesters were obtained from 3-hydroxy-1H-indole-2-carboxylic acid esters and methyl or ethyl bromoacetate. Reactions of the furo [3, 2-b] indole enolic esters prepared are discussed.

Formaldehyde Structure

2-anilino-5-methoxybenzoic acid Structure

2-anilino-5-met...

~83%

6-methoxy-1-phenyl-2H-3,1-benzoxazin-4-one Structure

6-methoxy-1-phe...

2-((2-methoxy-2-oxoethyl)phenylamino)benzoic acid methyl ester Structure

2-((2-methoxy-2...

~71%

methyl 3-hydroxy-1-phenylindole-2-carboxylate Structure

methyl 3-hydrox...

POTASSIUM CYANIDE Structure

POTASSIUM CYANIDE

6-methoxy-1-phenyl-2H-3,1-benzoxazin-4-one Structure

6-methoxy-1-phe...

~96%

2-[N-(cyanomethyl)anilino]-5-methoxybenzoic acid Structure

2-[N-(cyanometh...

2-anilino-5-methoxybenzoic acid Structure

2-anilino-5-met...

~%

2-[N-(cyanomethyl)anilino]-5-methoxybenzoic acid Structure

2-[N-(cyanometh...

2-anilino-5-methoxybenzoic acid Structure

2-anilino-5-met...

~%

2-[N-(carboxymethyl)anilino]-5-methoxybenzoic acid Structure

2-[N-(carboxyme...

6-methoxy-1-phenyl-2H-3,1-benzoxazin-4-one Structure

6-methoxy-1-phe...

~%

2-[N-(carboxymethyl)anilino]-5-methoxybenzoic acid Structure

2-[N-(carboxyme...

methyl 3-hydroxy-1-phenylindole-2-carboxylate Structure

methyl 3-hydrox...

~%

3-methoxy-4-phenylfuro[3,2-b]indole-2-carboxamide Structure

3-methoxy-4-phe...

2-[N-(carboxymethyl)anilino]benzoic acid Structure

2-[N-(carboxyme...

~%

3-methoxy-4-phenylfuro[3,2-b]indole-2-carboxamide Structure

3-methoxy-4-phe...

2-((2-methoxy-2-oxoethyl)phenylamino)benzoic acid methyl ester Structure

2-((2-methoxy-2...

~%

3-methoxy-4-phenylfuro[3,2-b]indole-2-carboxamide Structure

3-methoxy-4-phe...

N/A Structure

~%

3-methoxy-4-phenylfuro[3,2-b]indole-2-carboxamide Structure

3-methoxy-4-phe...

3-(2-methoxy-2-oxoethoxy)-1-phenyl-1H-indole-2-carboxylic acid methyl ester Structure

3-(2-methoxy-2-...

~%

3-methoxy-4-phenylfuro[3,2-b]indole-2-carboxamide Structure

3-methoxy-4-phe...

3,7-dimethoxy-4-phenyl-4H-furo<3,2-b>indole-2-carboxylic acid methyl ester Structure

3,7-dimethoxy-4...

~%

3,7-dimethoxy-4-phenylfuro[3,2-b]indole-2-carboxylic acid Structure

3,7-dimethoxy-4...

2-anilino-5-methoxybenzoic acid Structure

2-anilino-5-met...

~%

3,7-dimethoxy-4-phenylfuro[3,2-b]indole-2-carboxylic acid Structure

3,7-dimethoxy-4...

6-methoxy-1-phenyl-2H-3,1-benzoxazin-4-one Structure

6-methoxy-1-phe...

~%

3,7-dimethoxy-4-phenylfuro[3,2-b]indole-2-carboxylic acid Structure

3,7-dimethoxy-4...

3-hydroxy-5-methoxy-1-phenyl-1H-indole-2-carboxylic acid methyl ester Structure

3-hydroxy-5-met...

~%

3,7-dimethoxy-4-phenylfuro[3,2-b]indole-2-carboxylic acid Structure

3,7-dimethoxy-4...

2-[N-(carboxymethyl)anilino]-5-methoxybenzoic acid Structure

2-[N-(carboxyme...

~%

3,7-dimethoxy-4-phenylfuro[3,2-b]indole-2-carboxylic acid Structure

3,7-dimethoxy-4...

2-[N-(cyanomethyl)anilino]-5-methoxybenzoic acid Structure

2-[N-(cyanometh...

~%

3,7-dimethoxy-4-phenylfuro[3,2-b]indole-2-carboxylic acid Structure

3,7-dimethoxy-4...

3-hydroxy-7-methoxy-4-phenyl-4H-furo(3,2-b)indole-2-carboxylic acid methyl ester Structure

3-hydroxy-7-met...

~%

3,7-dimethoxy-4-phenylfuro[3,2-b]indole-2-carboxylic acid Structure

3,7-dimethoxy-4...

5-methoxy-3-(2-methoxy-2-oxoethoxy)-1-phenyl-1H-indole-2-carboxylic acid methyl ester Structure

5-methoxy-3-(2-...

~%

3,7-dimethoxy-4-phenylfuro[3,2-b]indole-2-carboxylic acid Structure

3,7-dimethoxy-4...

5-methoxy-2-((2-methoxy-2-oxoethyl)phenylamino)benzoic acid methyl ester Structure

5-methoxy-2-((2...

~%

3,7-dimethoxy-4-phenylfuro[3,2-b]indole-2-carboxylic acid Structure

3,7-dimethoxy-4...

methyl 3-hydroxy-1-phenylindole-2-carboxylate Structure

methyl 3-hydrox...

~%

3-methoxy-4-phenylfuro[3,2-b]indole-2-carboxylic acid Structure

3-methoxy-4-phe...

2-[N-(carboxymethyl)anilino]benzoic acid Structure

2-[N-(carboxyme...

~%

3-methoxy-4-phenylfuro[3,2-b]indole-2-carboxylic acid Structure

3-methoxy-4-phe...

2-((2-methoxy-2-oxoethyl)phenylamino)benzoic acid methyl ester Structure

2-((2-methoxy-2...

~%

3-methoxy-4-phenylfuro[3,2-b]indole-2-carboxylic acid Structure

3-methoxy-4-phe...

N/A Structure

~%

3-methoxy-4-phenylfuro[3,2-b]indole-2-carboxylic acid Structure

3-methoxy-4-phe...

3-(2-methoxy-2-oxoethoxy)-1-phenyl-1H-indole-2-carboxylic acid methyl ester Structure

3-(2-methoxy-2-...

~%

3-methoxy-4-phenylfuro[3,2-b]indole-2-carboxylic acid Structure

3-methoxy-4-phe...

N/A Structure

~%

3-methoxy-4-methylfuro[3,2-b]indole-2-carboxylic acid Structure

3-methoxy-4-met...

3-(2-ethoxy-2-oxoethoxy)-1-methyl-1H-indole-2-carboxylic acid ethyl ester Structure

3-(2-ethoxy-2-o...

~%

3-methoxy-4-methylfuro[3,2-b]indole-2-carboxylic acid Structure

3-methoxy-4-met...

ethyl 3-hydroxy-1-methylindole-2-carboxylate Structure

ethyl 3-hydroxy...

~%

3-methoxy-4-methylfuro[3,2-b]indole-2-carboxylic acid Structure

3-methoxy-4-met...

methyl 3-hydroxy-1-phenylindole-2-carboxylate Structure

methyl 3-hydrox...

~%

3-ethoxy-4-phenylfuro[3,2-b]indole-2-carboxylic acid Structure

3-ethoxy-4-phen...

2-[N-(carboxymethyl)anilino]benzoic acid Structure

2-[N-(carboxyme...

~%

3-ethoxy-4-phenylfuro[3,2-b]indole-2-carboxylic acid Structure

3-ethoxy-4-phen...

2-((2-methoxy-2-oxoethyl)phenylamino)benzoic acid methyl ester Structure

2-((2-methoxy-2...

~%

3-ethoxy-4-phenylfuro[3,2-b]indole-2-carboxylic acid Structure

3-ethoxy-4-phen...

N/A Structure

~%

3-ethoxy-4-phenylfuro[3,2-b]indole-2-carboxylic acid Structure

3-ethoxy-4-phen...

3-(2-methoxy-2-oxoethoxy)-1-phenyl-1H-indole-2-carboxylic acid methyl ester Structure

3-(2-methoxy-2-...

~%

3-ethoxy-4-phenylfuro[3,2-b]indole-2-carboxylic acid Structure

3-ethoxy-4-phen...

methyl 3-hydroxy-1-phenylindole-2-carboxylate Structure

methyl 3-hydrox...

~%

3-ethoxy-4-phenylfuro[3,2-b]indole-2-carboxamide Structure

3-ethoxy-4-phen...

2-[N-(carboxymethyl)anilino]benzoic acid Structure

2-[N-(carboxyme...

~%

3-ethoxy-4-phenylfuro[3,2-b]indole-2-carboxamide Structure

3-ethoxy-4-phen...

2-((2-methoxy-2-oxoethyl)phenylamino)benzoic acid methyl ester Structure

2-((2-methoxy-2...

~%

3-ethoxy-4-phenylfuro[3,2-b]indole-2-carboxamide Structure

3-ethoxy-4-phen...

N/A Structure

~%

3-ethoxy-4-phenylfuro[3,2-b]indole-2-carboxamide Structure

3-ethoxy-4-phen...

3-(2-methoxy-2-oxoethoxy)-1-phenyl-1H-indole-2-carboxylic acid methyl ester Structure

3-(2-methoxy-2-...

~%

3-ethoxy-4-phenylfuro[3,2-b]indole-2-carboxamide Structure

3-ethoxy-4-phen...

3-methoxy-4-methyl-4H-furo(3,2-b)indole-2-carboxylic acid ethyl ester Structure

3-methoxy-4-met...

~78%

3-methoxy-4-methylfuro[3,2-b]indole-2-carboxamide Structure

3-methoxy-4-met...

N/A Structure

~%

3-methoxy-4-methylfuro[3,2-b]indole-2-carboxamide Structure

3-methoxy-4-met...

3-(2-ethoxy-2-oxoethoxy)-1-methyl-1H-indole-2-carboxylic acid ethyl ester Structure

3-(2-ethoxy-2-o...

~%

3-methoxy-4-methylfuro[3,2-b]indole-2-carboxamide Structure

3-methoxy-4-met...

ethyl 3-hydroxy-1-methylindole-2-carboxylate Structure

ethyl 3-hydroxy...

~%

3-methoxy-4-methylfuro[3,2-b]indole-2-carboxamide Structure

3-methoxy-4-met...

3-ethoxy-7-methoxy-4-phenyl-4H-furo(3,2-b)indole-2-carboxylic acid methyl ester Structure

3-ethoxy-7-meth...

~%

3-ethoxy-7-methoxy-4-phenylfuro[3,2-b]indole-2-carboxylic acid Structure

3-ethoxy-7-meth...

methyl 3-hydroxy-1-phenylindole-2-carboxylate Structure

methyl 3-hydrox...

~%

3-ethoxy-7-methoxy-4-phenylfuro[3,2-b]indole-2-carboxylic acid Structure

3-ethoxy-7-meth...

2-[N-(carboxymethyl)anilino]benzoic acid Structure

2-[N-(carboxyme...

~%

3-ethoxy-7-methoxy-4-phenylfuro[3,2-b]indole-2-carboxylic acid Structure

3-ethoxy-7-meth...

2-((2-methoxy-2-oxoethyl)phenylamino)benzoic acid methyl ester Structure

2-((2-methoxy-2...

~%

3-ethoxy-7-methoxy-4-phenylfuro[3,2-b]indole-2-carboxylic acid Structure

3-ethoxy-7-meth...

N/A Structure

~%

3-ethoxy-7-methoxy-4-phenylfuro[3,2-b]indole-2-carboxylic acid Structure

3-ethoxy-7-meth...

3-(2-methoxy-2-oxoethoxy)-1-phenyl-1H-indole-2-carboxylic acid methyl ester Structure

3-(2-methoxy-2-...

~%

3-ethoxy-7-methoxy-4-phenylfuro[3,2-b]indole-2-carboxylic acid Structure

3-ethoxy-7-meth...

2-anilino-5-methoxybenzoic acid Structure

2-anilino-5-met...

~%

3,7-dimethoxy-4-phenylfuro[3,2-b]indole-2-carboxamide Structure

3,7-dimethoxy-4...

6-methoxy-1-phenyl-2H-3,1-benzoxazin-4-one Structure

6-methoxy-1-phe...

~%

3,7-dimethoxy-4-phenylfuro[3,2-b]indole-2-carboxamide Structure

3,7-dimethoxy-4...

3-hydroxy-5-methoxy-1-phenyl-1H-indole-2-carboxylic acid methyl ester Structure

3-hydroxy-5-met...

~%

3,7-dimethoxy-4-phenylfuro[3,2-b]indole-2-carboxamide Structure

3,7-dimethoxy-4...

2-[N-(carboxymethyl)anilino]-5-methoxybenzoic acid Structure

2-[N-(carboxyme...

~%

3,7-dimethoxy-4-phenylfuro[3,2-b]indole-2-carboxamide Structure

3,7-dimethoxy-4...

2-[N-(cyanomethyl)anilino]-5-methoxybenzoic acid Structure

2-[N-(cyanometh...

~%

3,7-dimethoxy-4-phenylfuro[3,2-b]indole-2-carboxamide Structure

3,7-dimethoxy-4...

3-hydroxy-7-methoxy-4-phenyl-4H-furo(3,2-b)indole-2-carboxylic acid methyl ester Structure

3-hydroxy-7-met...

~%

3,7-dimethoxy-4-phenylfuro[3,2-b]indole-2-carboxamide Structure

3,7-dimethoxy-4...

5-methoxy-3-(2-methoxy-2-oxoethoxy)-1-phenyl-1H-indole-2-carboxylic acid methyl ester Structure

5-methoxy-3-(2-...

~%

3,7-dimethoxy-4-phenylfuro[3,2-b]indole-2-carboxamide Structure

3,7-dimethoxy-4...

5-methoxy-2-((2-methoxy-2-oxoethyl)phenylamino)benzoic acid methyl ester Structure

5-methoxy-2-((2...

~%

3,7-dimethoxy-4-phenylfuro[3,2-b]indole-2-carboxamide Structure

3,7-dimethoxy-4...