Intermediates Formed in the Reaction of Benzenethiol or t-Butylthiobenzene with Ethyl Benzoylacetate in Polyphosphoric Acid

H Nakazumi, S Watanabe, T Kitaguchi…

Index: Nakazumi; Watanabe; Kitaguchi; Kitao Bulletin of the Chemical Society of Japan, 1990 , vol. 63, # 3 p. 847 - 851

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Citation Number: 11

Abstract

The reaction of benzenethiol with ethyl benzoylacetate in polyphosphoric acid (PPA) at low temperature gave mainly ethyl 3-phenyl-3, 3-bis (phenylthio) propionate 8 as an intermediate in the synthesis of thioflavones, while that from t-butylthiobenzene under similar conditions gave ethyl 3-(phenylthio) cinnamate 7 as a major product and many by-products. The reaction constant for intramolecular cyclic condensation of 7 in 98% sulfuric acid was ...

 Related Synthetic Route
ethyl (Z)-3-((4-methoxyphenyl)thio)cinnamate Structure

84144-37-6

ethyl (Z)-3-((4...

~%

6-methoxy-2-phenyl-thiochromen-4-one Structure

789-98-0

6-methoxy-2-phe...

4-methoxyphenyl 2-methyl-2-propyl sulfide Structure

7205-64-3

4-methoxyphenyl...

Ethyl 3-oxo-3-phenylpropanoate Structure

94-02-0

Ethyl 3-oxo-3-p...

~2%

6-methoxy-2-phenyl-thiochromen-4-one Structure

789-98-0

6-methoxy-2-phe...

N/A Structure

128671-23-8

N/A

Detail
Ethyl (Z)-3-(4-acetylphenylthio)cinnamate Structure

128671-32-9

Ethyl (Z)-3-(4-...

~%

6-methoxy-2-phenyl-thiochromen-4-one Structure

789-98-0

6-methoxy-2-phe...

ethyl 3-chloro-3-phenylprop-2-enoate Structure

55164-19-7

ethyl 3-chloro-...

~%

6-methoxy-2-phenyl-thiochromen-4-one Structure

789-98-0

6-methoxy-2-phe...

Ethyl (Z)-3-(4-acetylphenylthio)cinnamate Structure

128671-32-9

Ethyl (Z)-3-(4-...

~74%

4-MERCAPTOACETOPHENONE Structure

3814-20-8

4-MERCAPTOACETO...

3-Hydroxy-1-indenone Structure

70432-32-5

3-Hydroxy-1-indenone

Ethyl 3-oxo-3-phenylpropanoate Structure

94-02-0

Ethyl 3-oxo-3-p...

tert-Butyl(4-methylphenyl) sulfide Structure

7439-10-3

tert-Butyl(4-me...

Ethyl 3-oxo-3-phenylpropanoate Structure

94-02-0

Ethyl 3-oxo-3-p...

~11%

4H-1-Benzothiopyran-4-one,6-methyl-2-phenyl- Structure

787-44-0

4H-1-Benzothiop...

cis-β-p-Tolylthio-zimtsaeureethylester Structure

34875-14-4

cis-β-p-Tolylth...

Detail
β-p-tolylsulfanyl-trans-cinnamic acid ethyl ester Structure

34875-04-2

β-p-tolylsulfan...

~%

4H-1-Benzothiopyran-4-one,6-methyl-2-phenyl- Structure

787-44-0

4H-1-Benzothiop...

Ethyl (Z)-3-(4-acetylphenylthio)cinnamate Structure

128671-32-9

Ethyl (Z)-3-(4-...

~%

4H-1-Benzothiopyran-4-one,6-methyl-2-phenyl- Structure

787-44-0

4H-1-Benzothiop...

ethyl 3-chloro-3-phenylprop-2-enoate Structure

55164-19-7

ethyl 3-chloro-...

~%

4H-1-Benzothiopyran-4-one,6-methyl-2-phenyl- Structure

787-44-0

4H-1-Benzothiop...

Ethyl 3-phenyl-3,3-bis(phenylthio)propionate Structure

75794-13-7

Ethyl 3-phenyl-...

~97%

1-THIOFLAVONE Structure

784-62-3

1-THIOFLAVONE

β-phenylsulfanyl-cinnamic acid ethyl ester Structure

34875-02-0

β-phenylsulfany...

~97%

1-THIOFLAVONE Structure

784-62-3

1-THIOFLAVONE

Phenyl tert-butyl sulfide Structure

3019-19-0

Phenyl tert-but...

Ethyl 3-oxo-3-phenylpropanoate Structure

94-02-0

Ethyl 3-oxo-3-p...

~21%

1-THIOFLAVONE Structure

784-62-3

1-THIOFLAVONE

β-phenylsulfanyl-cinnamic acid ethyl ester Structure

34875-12-2

β-phenylsulfany...

Detail
Ethyl (Z)-3-(4-acetylphenylthio)cinnamate Structure

128671-32-9

Ethyl (Z)-3-(4-...

~%

1-THIOFLAVONE Structure

784-62-3

1-THIOFLAVONE

ethyl 3-chloro-3-phenylprop-2-enoate Structure

55164-19-7

ethyl 3-chloro-...

~%

1-THIOFLAVONE Structure

784-62-3

1-THIOFLAVONE

Ethyl 3-oxo-3-phenylpropanoate Structure

94-02-0

Ethyl 3-oxo-3-p...

~%

1-THIOFLAVONE Structure

784-62-3

1-THIOFLAVONE

Phenyl tert-butyl sulfide Structure

3019-19-0

Phenyl tert-but...

~%

1-THIOFLAVONE Structure

784-62-3

1-THIOFLAVONE


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