Tetrahedron

Synthesis of activated 3-substituted indoles: an optimised one-pot procedure

K Pchalek, AW Jones, MMT Wekking, DSC Black

Index: Pchalek, Karin; Jones, Ashley W.; Wekking, Monique M.T.; Black, David StC. Tetrahedron, 2005 , vol. 61, # 1 p. 77 - 82

Full Text: HTML

Citation Number: 42

Abstract

Download PDF Opens in a new window. Article suggestions will be shown in a dialog on return to ScienceDirect. ... Please enable JavaScript to use all the features on this page. ... 3-Substituted-4,6-dimethoxyindoles can be synthesised in a one-pot procedure from 3,5-dimethoxyaniline and 2-haloketones in the presence of lithium bromide and sodium bicarbonate. ... The indole nucleus is present in a wide range of natural products, and consequently a variety of ...

 Related Synthetic Route
1-(4,6-dimethoxy-3-methylindol-1-yl)ethanone Structure

827024-88-4

1-(4,6-dimethox...

~89%

4,6-dimethoxy-3-methyl-1H-indole Structure

74973-30-1

4,6-dimethoxy-3...

Chloroacetone Structure

78-95-5

Chloroacetone

3,5-Dimethoxyaniline Structure

10272-07-8

3,5-Dimethoxyaniline

~76%

4,6-dimethoxy-3-methyl-1H-indole Structure

74973-30-1

4,6-dimethoxy-3...

3,5-Dimethoxyaniline Structure

10272-07-8

3,5-Dimethoxyaniline

~%

4,6-dimethoxy-3-methyl-1H-indole Structure

74973-30-1

4,6-dimethoxy-3...

1-(3,5-dimethoxyanilino)propan-2-one Structure

827024-98-6

1-(3,5-dimethox...

~%

4,6-dimethoxy-3-methyl-1H-indole Structure

74973-30-1

4,6-dimethoxy-3...

3,5-Dimethoxyaniline Structure

10272-07-8

3,5-Dimethoxyaniline

~%

1-(4,6-dimethoxy-3-methylindol-1-yl)ethanone Structure

827024-88-4

1-(4,6-dimethox...

1-(3,5-dimethoxyanilino)propan-2-one Structure

827024-98-6

1-(3,5-dimethox...

~%

1-(4,6-dimethoxy-3-methylindol-1-yl)ethanone Structure

827024-88-4

1-(4,6-dimethox...

2-Bromoacetophenone Structure

70-11-1

2-Bromoacetophenone

3,5-Dimethoxyaniline Structure

10272-07-8

3,5-Dimethoxyaniline

~15%

4,6-dimethoxy-2-phenyl-1H-indole Structure

74794-89-1

4,6-dimethoxy-2...

4,6-dimethoxy-3-phenyl-1H-indole Structure

105776-29-2

4,6-dimethoxy-3...

Detail
2-Bromoacetophenone Structure

70-11-1

2-Bromoacetophenone

3,5-Dimethoxyaniline Structure

10272-07-8

3,5-Dimethoxyaniline

~0%

4,6-dimethoxy-2-phenyl-1H-indole Structure

74794-89-1

4,6-dimethoxy-2...

4,6-dimethoxy-3-phenyl-1H-indole Structure

105776-29-2

4,6-dimethoxy-3...

Detail
Ethyl 2-Chloroacetoacetate Structure

638-07-3

Ethyl 2-Chloroa...

~%

ethyl 2-(1-acetyl-4,6-dimethoxyindol-3-yl)acetate Structure

827024-90-8

ethyl 2-(1-acet...

3,5-Dimethoxyaniline Structure

10272-07-8

3,5-Dimethoxyaniline

~%

ethyl 2-(1-acetyl-4,6-dimethoxyindol-3-yl)acetate Structure

827024-90-8

ethyl 2-(1-acet...

2-Bromo-4'-hydroxyacetophenone Structure

2491-38-5

2-Bromo-4'-hydr...

3,5-Dimethoxyaniline Structure

10272-07-8

3,5-Dimethoxyaniline

~56%

2-(3,5-dimethoxyanilino)-1-(4-hydroxyphenyl)ethanone Structure

827024-96-4

2-(3,5-dimethox...

2-(N-acetyl-3,5-dimethoxyphenylamino)-1-(4-hydroxyphenyl)ethanone Structure

827024-87-3

2-(N-acetyl-3,5...

~80%

1-[3-(4-hydroxyphenyl)-4,6-dimethoxyindol-1-yl]ethanone Structure

827024-97-5

1-[3-(4-hydroxy...

2-Bromo-4'-hydroxyacetophenone Structure

2491-38-5

2-Bromo-4'-hydr...

~%

1-[3-(4-hydroxyphenyl)-4,6-dimethoxyindol-1-yl]ethanone Structure

827024-97-5

1-[3-(4-hydroxy...

3,5-Dimethoxyaniline Structure

10272-07-8

3,5-Dimethoxyaniline

~%

1-[3-(4-hydroxyphenyl)-4,6-dimethoxyindol-1-yl]ethanone Structure

827024-97-5

1-[3-(4-hydroxy...

2-(3,5-dimethoxyanilino)-1-(4-hydroxyphenyl)ethanone Structure

827024-96-4

2-(3,5-dimethox...

~%

1-[3-(4-hydroxyphenyl)-4,6-dimethoxyindol-1-yl]ethanone Structure

827024-97-5

1-[3-(4-hydroxy...


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