Synlett

Synthesis of Functionalized 1, 4-Dihydro-9, 10-anthraquinones and Anthraquinones by Ring Closing Metathesis Using Grubbs' Catalyst

TN Van, M D'hooghe, S Pattyn, N De Kimpe

Index: Van Nguyen, Tuyen; D'Hooghe, Matthias; Pattyn, Siegfried; De Kimpe, Norbert Synlett, 2004 , # 11 p. 1913 - 1916

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Abstract

Abstract A general and straightforward synthesis of anthraquinones was developed, in which diallylation of 1, 4-naphthoquinones, followed by Ring Closing Metathesis (RCM) of the resulting diallylnaphthoquinones with Grubbs' catalyst and subsequent dehydrogenation using Pd/C afforded the desired anthraquinones with regiocontrol of substituents and in good yields.

 Related Synthetic Route
1-methyl-1,4-dihydro-9,10-anthraquinone Structure

32740-63-9

1-methyl-1,4-di...

~88%

.alpha.-Methylanthraquinone Structure

954-07-4

.alpha.-Methyla...

1,4-naphthoquinone Structure

130-15-4

1,4-naphthoquinone

~%

.alpha.-Methylanthraquinone Structure

954-07-4

.alpha.-Methyla...

4-Methoxy-1-naphthol Structure

84-85-5

4-Methoxy-1-naphthol

~%

.alpha.-Methylanthraquinone Structure

954-07-4

.alpha.-Methyla...

2-but-3-en-2-ylnaphthalene-1,4-dione Structure

74785-26-5

2-but-3-en-2-yl...

~%

.alpha.-Methylanthraquinone Structure

954-07-4

.alpha.-Methyla...

(E)-1-(2'-butenoxy)-4-methoxynaphthalene Structure

786653-55-2

(E)-1-(2'-buten...

~%

.alpha.-Methylanthraquinone Structure

954-07-4

.alpha.-Methyla...

2-allyl-3-(but-3-en-2-yl)naphthalene-1,4-dione Structure

786653-56-3

2-allyl-3-(but-...

~%

.alpha.-Methylanthraquinone Structure

954-07-4

.alpha.-Methyla...

2,3-diallyl-1,4-naphthoquinone Structure

716320-09-1

2,3-diallyl-1,4...

~86%

1,4-dihydroanthracene-9,10-dione Structure

885-19-8

1,4-dihydroanth...

1,4-naphthoquinone Structure

130-15-4

1,4-naphthoquinone

~%

1,4-dihydroanthracene-9,10-dione Structure

885-19-8

1,4-dihydroanth...

4-Methoxy-1-naphthol Structure

84-85-5

4-Methoxy-1-naphthol

~%

2-but-3-en-2-ylnaphthalene-1,4-dione Structure

74785-26-5

2-but-3-en-2-yl...

1,4-naphthoquinone Structure

130-15-4

1,4-naphthoquinone

~%

2-but-3-en-2-ylnaphthalene-1,4-dione Structure

74785-26-5

2-but-3-en-2-yl...

(E)-1-(2'-butenoxy)-4-methoxynaphthalene Structure

786653-55-2

(E)-1-(2'-buten...

~%

2-but-3-en-2-ylnaphthalene-1,4-dione Structure

74785-26-5

2-but-3-en-2-yl...

N/A Structure

100914-89-4

N/A

~94%

1-Methoxyanthraquinone Structure

82-39-3

1-Methoxyanthra...

5-methoxynaphthalene-1,4-dione Structure

4923-61-9

5-methoxynaphth...

~%

1-Methoxyanthraquinone Structure

82-39-3

1-Methoxyanthra...

Juglone Structure

481-39-0

Juglone

~%

1-Methoxyanthraquinone Structure

82-39-3

1-Methoxyanthra...

2,3-diallyl-5-methoxynaphthalene-1,4-dione Structure

786653-54-1

2,3-diallyl-5-m...

~%

1-Methoxyanthraquinone Structure

82-39-3

1-Methoxyanthra...

N/A Structure

99397-96-3

N/A

~96%

1-HYDROXYANTHRAQUINONE Structure

129-43-1

1-HYDROXYANTHRA...


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