Tetrahedron

Regioselective synthesis of flavone derivatives via DMAP-catalyzed cyclization of o-alkynoylphenols

M Yoshida, Y Fujino, K Saito, T Doi

Index: Yoshida, Masahito; Fujino, Yuta; Saito, Koya; Doi, Takayuki Tetrahedron, 2011 , vol. 67, # 51 p. 9993 - 9997

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Citation Number: 30

Abstract

A catalytic amount of DMAP promoted cyclization of o-alkynoylphenols via a 6-endo cyclization mode leading to flavone derivatives in high yields without forming 5-exo cyclized aurone derivatives. Utilizing this method, methoxy substituted flavone and alkyl substituted γ- benzopyranone derivatives were synthesized.

 Related Synthetic Route
1-(2-hydroxy-5-methoxyphenyl)-3-phenylprop-2-yn-1-one Structure

104213-88-9

1-(2-hydroxy-5-...

~91%

6-Methoxyflavone Structure

26964-24-9

6-Methoxyflavone

2-Hydroxy-5-methoxybenzaldehyde Structure

672-13-9

2-Hydroxy-5-met...

~%

6-Methoxyflavone Structure

26964-24-9

6-Methoxyflavone

Phenylacetylene Structure

536-74-3

Phenylacetylene

~%

6-Methoxyflavone Structure

26964-24-9

6-Methoxyflavone

N/A Structure

133503-46-5

N/A

~%

1-(2-hydroxy-5-methoxyphenyl)-3-phenylprop-2-yn-1-one Structure

104213-88-9

1-(2-hydroxy-5-...

Phenylacetylene Structure

536-74-3

Phenylacetylene

~%

1-(2-hydroxy-5-methoxyphenyl)-3-phenylprop-2-yn-1-one Structure

104213-88-9

1-(2-hydroxy-5-...

6-methoxy-2-[3-phenylpropynoyl]phenol Structure

1322774-91-3

6-methoxy-2-[3-...

~91%

8-Methoxy-2-phenylchromone Structure

26964-26-1

8-Methoxy-2-phe...

3-Methoxysalicylaldehyde Structure

148-53-8

3-Methoxysalicy...

~%

8-Methoxy-2-phenylchromone Structure

26964-26-1

8-Methoxy-2-phe...

Phenylacetylene Structure

536-74-3

Phenylacetylene

~%

8-Methoxy-2-phenylchromone Structure

26964-26-1

8-Methoxy-2-phe...

2-Hydroxy-5-methoxybenzaldehyde Structure

672-13-9

2-Hydroxy-5-met...

~%

1-(2-hydroxy-5-methoxyphenyl)-3-phenylprop-2-yn-1-one Structure

104213-88-9

1-(2-hydroxy-5-...

1-(2-hydroxyphenyl)-3-(4-methoxyphenyl)prop-2-yn-1-one Structure

101278-20-0

1-(2-hydroxyphe...

~90%

4'-Methoxyflavone Structure

4143-74-2

4'-Methoxyflavone

Salicylaldehyde Structure

90-02-8

Salicylaldehyde

~%

4'-Methoxyflavone Structure

4143-74-2

4'-Methoxyflavone

4-Ethynylanisole Structure

768-60-5

4-Ethynylanisole

~%

4'-Methoxyflavone Structure

4143-74-2

4'-Methoxyflavone

N/A Structure

128216-91-1

N/A

~20%

5-Methoxyflavone Structure

42079-78-7

5-Methoxyflavone

4-methoxyaurone Structure

57060-62-5

4-methoxyaurone

2-Hydroxy-6-methoxybenzaldehyde Structure

700-44-7

2-Hydroxy-6-met...

~%

5-Methoxyflavone Structure

42079-78-7

5-Methoxyflavone

4-methoxyaurone Structure

57060-62-5

4-methoxyaurone

2-(1-hydroxy-3-phenylprop-2-yn-1-yl)-3-methoxyphenol Structure

1322775-81-4

2-(1-hydroxy-3-...

~%

5-Methoxyflavone Structure

42079-78-7

5-Methoxyflavone

4-methoxyaurone Structure

57060-62-5

4-methoxyaurone

Phenylacetylene Structure

536-74-3

Phenylacetylene

~%

5-Methoxyflavone Structure

42079-78-7

5-Methoxyflavone

4-methoxyaurone Structure

57060-62-5

4-methoxyaurone

5-methoxy-2-[3-(4-methoxyphenyl)propynoyl]phenol Structure

107275-22-9

5-methoxy-2-[3-...

~74%

7,4'-DIMETHOXYFLAVONE Structure

20979-50-4

7,4'-DIMETHOXYF...


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