Bulletin of the Chemical Society of Japan

Studies of the Selective O-Alkylation and Dealkylation of Flavonoids. XV. A Convenient Synthesis of 3, 5, 6-Trihydroxy-7-methoxyflavones and Revised Structures of …

H Tominaga, T Horie

Index: Tominaga; Horie Bulletin of the Chemical Society of Japan, 1993 , vol. 66, # 9 p. 2668 - 2675

Full Text: HTML

Citation Number: 6

Abstract

A mixture of 6-hydroxy-3, 4′, 5, 7-tetramethoxy-and 5, 6-dihydroxy-3, 4′, 7- trimethoxyflavone was converted into 6-acetoxy-5-hydroxy-3, 4′, 7-trimethoxyflavone by acetylation and following dealkylation. The 3-methoxyl group in the tosylate of the 5- hydroxyflavone was selectively cleaved with anhydrous aluminum bromide in acetonitrile to give 6-acetoxy-3-hydroxy-4′, 7-dimethoxy-5-(tosyloxy) flavone. 3, 6-Dihydroxy-4′, 7- ...

 Related Synthetic Route
5,6-dihydroxy-3,4',7-trimethoxyflavone diacetate Structure

154047-82-2

5,6-dihydroxy-3...

~%

3,5,6-trihydroxy-7-methoxy-2-(4-methoxyphenyl)chromen-4-one Structure

99499-82-8

3,5,6-trihydrox...

N/A Structure

154047-87-7

N/A

~%

3,5,6-trihydroxy-7-methoxy-2-(4-methoxyphenyl)chromen-4-one Structure

99499-82-8

3,5,6-trihydrox...

3-hydroxy-7-methoxy-2-(4-methoxyphenyl)-4-oxo-5-(tosyloxy)-4H-chromen-6-yl acetate Structure

154048-03-0

3-hydroxy-7-met...

~%

3,5,6-trihydroxy-7-methoxy-2-(4-methoxyphenyl)chromen-4-one Structure

99499-82-8

3,5,6-trihydrox...

N/A Structure

154047-95-7

N/A

~%

3,5,6-trihydroxy-7-methoxy-2-(4-methoxyphenyl)chromen-4-one Structure

99499-82-8

3,5,6-trihydrox...

3,5-dihydroxy-7-methoxy-6-(methoxymethoxy)-2-(4-methoxyphenyl)-4H-chromen-4-one Structure

154048-27-8

3,5-dihydroxy-7...

~%

3,5,6-trihydroxy-7-methoxy-2-(4-methoxyphenyl)chromen-4-one Structure

99499-82-8

3,5,6-trihydrox...

3,6-dihydroxy-7-methoxy-2-(4-methoxyphenyl)-4-oxo-4H-chromen-5-yl 4-methylbenzenesulfonate Structure

154048-11-0

3,6-dihydroxy-7...

~%

3,5,6-trihydroxy-7-methoxy-2-(4-methoxyphenyl)chromen-4-one Structure

99499-82-8

3,5,6-trihydrox...

2-(3,4-dimethoxyphenyl)-3-hydroxy-7-methoxy-4-oxo-5-(tosyloxy)-4H-chromen-6-yl acetate Structure

154048-04-1

2-(3,4-dimethox...

~%

2-(3,4-dimethoxyphenyl)-3,5,6-trihydroxy-7-methoxychromen-4-one Structure

99499-83-9

2-(3,4-dimethox...

N/A Structure

154047-96-8

N/A

~%

2-(3,4-dimethoxyphenyl)-3,5,6-trihydroxy-7-methoxychromen-4-one Structure

99499-83-9

2-(3,4-dimethox...

2-(3,4-dimethoxyphenyl)-3,5-dihydroxy-7-methoxy-6-(methoxymethoxy)-4H-chromen-4-one Structure

154048-28-9

2-(3,4-dimethox...

~%

2-(3,4-dimethoxyphenyl)-3,5,6-trihydroxy-7-methoxychromen-4-one Structure

99499-83-9

2-(3,4-dimethox...

2-(3,4-dimethoxyphenyl)-3,6-dihydroxy-7-methoxy-4-oxo-4H-chromen-5-yl 4-methylbenzenesulfonate Structure

154048-12-1

2-(3,4-dimethox...

~%

2-(3,4-dimethoxyphenyl)-3,5,6-trihydroxy-7-methoxychromen-4-one Structure

99499-83-9

2-(3,4-dimethox...

5,8-Dihydroxy-3,4',7-trimethoxyflavone Structure

58902-16-2

5,8-Dihydroxy-3...

~%

3,5,8-trihydroxy-7,4'-dimethoxyflavone Structure

70703-48-9

3,5,8-trihydrox...

5-hydroxy-3,7-dimethoxy-8-(methoxymethoxy)-2-(4-methoxyphenyl)-4H-chromen-4-one Structure

154048-48-3

5-hydroxy-3,7-d...

~%

3,5,8-trihydroxy-7,4'-dimethoxyflavone Structure

70703-48-9

3,5,8-trihydrox...

N/A Structure

154048-52-9

N/A

~%

3,5,8-trihydroxy-7,4'-dimethoxyflavone Structure

70703-48-9

3,5,8-trihydrox...

N/A Structure

154048-54-1

N/A

~%

3,5,8-trihydroxy-7,4'-dimethoxyflavone Structure

70703-48-9

3,5,8-trihydrox...

3,7-dimethoxy-8-(methoxymethoxy)-2-(4-methoxyphenyl)-4-oxo-4H-chromen-5-yl 4-methylbenzenesulfonate Structure

154048-50-7

3,7-dimethoxy-8...

~%

3,5,8-trihydroxy-7,4'-dimethoxyflavone Structure

70703-48-9

3,5,8-trihydrox...


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