Transacylation of α-Aryl-β-keto Esters

…, F Hidaka, S Shimizu, M Tamura, K Hori…

Index: Nishiwaki, Nagatoshi; Nishida, Daisei; Ohnishi, Tetsuya; Hidaka, Fumie; Shimizu, Satoru; Tamura, Mina; Hori, Kazushige; Tohda, Yasuo; Ariga, Masahiro Journal of Organic Chemistry, 2003 , vol. 68, # 22 p. 8650 - 8656

Full Text: HTML

Citation Number: 20

Abstract

The acyl group of an α-aryl-β-keto ester was readily transferred to N-, O-, and S- nucleophiles. The transacylation from arylated diethyl 3-oxoglutarate to amines led to unsymmetrical malonic acid amide esters in high yields. The present reaction proceeded under mild conditions without formation of detectable byproducts. Only simple experimental manipulations were required. This reaction was also found to be sensitive to steric factors, ...

 Related Synthetic Route
morpholine Structure

110-91-8

morpholine

N/A Structure

124089-63-0

N/A

~89%

N-Acetylmorpholine Structure

1696-20-4

N-Acetylmorpholine

ethyl 2-(2,4-dinitrophenyl)acetate Structure

68084-17-3

ethyl 2-(2,4-di...

Learn More
Ethyl 3-oxoglutarate Structure

105-50-0

Ethyl 3-oxoglutarate

~%

Propanoic acid,3-[(1,1-dimethylethyl)amino]-3-oxo-, ethyl ester Structure

17797-87-4

Propanoic acid,...

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N/A Structure

124089-63-0

N/A

isopropylamine Structure

75-31-0

isopropylamine

~95%

N-Isopropylacetamide Structure

1118-69-0

N-Isopropylacetamide

ethyl 2-(2,4-dinitrophenyl)acetate Structure

68084-17-3

ethyl 2-(2,4-di...

Learn More
Ethyl 3-oxoglutarate Structure

105-50-0

Ethyl 3-oxoglutarate

~%

ethyl 3-oxo-3-(propylamino)propanoate Structure

71510-96-8

ethyl 3-oxo-3-(...

Learn More
Ethyl 3-oxoglutarate Structure

105-50-0

Ethyl 3-oxoglutarate

~%

ethyl 3-(4-methoxyanilino)-3-oxopropanoate Structure

5382-15-0

ethyl 3-(4-meth...

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p-Anisidine Structure

104-94-9

p-Anisidine

N/A Structure

124089-63-0

N/A

~98%

ethyl 2-(2,4-dinitrophenyl)acetate Structure

68084-17-3

ethyl 2-(2,4-di...

4'-Methoxyacetanilide Structure

51-66-1

4'-Methoxyaceta...

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N/A Structure

124089-63-0

N/A

Structure

74497-02-2

~76%

ethyl 2-(2,4-dinitrophenyl)acetate Structure

68084-17-3

ethyl 2-(2,4-di...

Acetanilide Structure

103-84-4

Acetanilide

Learn More
N/A Structure

124089-63-0

N/A

Structure

74497-02-2

~0%

ethyl 2-(2,4-dinitrophenyl)acetate Structure

68084-17-3

ethyl 2-(2,4-di...

Acetanilide Structure

103-84-4

Acetanilide

Learn More
N/A Structure

124089-63-0

N/A

Ethanethiol Structure

75-08-1

Ethanethiol

~0%

Ethyl thioacetate Structure

625-60-5

Ethyl thioacetate

ethyl 2-(2,4-dinitrophenyl)acetate Structure

68084-17-3

ethyl 2-(2,4-di...

Learn More
Ethanol Structure

64-17-5

Ethanol

N/A Structure

124089-63-0

N/A

~0%

ethyl 2-(2,4-dinitrophenyl)acetate Structure

68084-17-3

ethyl 2-(2,4-di...

ethyl acetate Structure

141-78-6

ethyl acetate

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Pyrrolidine Structure

123-75-1

Pyrrolidine

N/A Structure

124089-63-0

N/A

~0%

N-Acetylpyrrolidine Structure

4030-18-6

N-Acetylpyrrolidine

ethyl 2-(2,4-dinitrophenyl)acetate Structure

68084-17-3

ethyl 2-(2,4-di...

Learn More
morpholine Structure

110-91-8

morpholine

N/A Structure

124089-63-0

N/A

~0%

N-Acetylmorpholine Structure

1696-20-4

N-Acetylmorpholine

ethyl 2-(2,4-dinitrophenyl)acetate Structure

68084-17-3

ethyl 2-(2,4-di...

Learn More
Propylamine Structure

107-10-8

Propylamine

N/A Structure

124089-63-0

N/A

~92%

Acetamide, N-propyl Structure

5331-48-6

Acetamide, N-propyl

ethyl 2-(2,4-dinitrophenyl)acetate Structure

68084-17-3

ethyl 2-(2,4-di...

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3,3-DIMETHYL-1-BUTANOL Structure

624-95-3

3,3-DIMETHYL-1-...

N/A Structure

124089-63-0

N/A

~0%

3,3-dimethylbutylacetate Structure

1421-87-0

3,3-dimethylbut...

ethyl 2-(2,4-dinitrophenyl)acetate Structure

68084-17-3

ethyl 2-(2,4-di...

Learn More
p-Anisidine Structure

104-94-9

p-Anisidine

N/A Structure

124089-63-0

N/A

~0%

ethyl 2-(2,4-dinitrophenyl)acetate Structure

68084-17-3

ethyl 2-(2,4-di...

4'-Methoxyacetanilide Structure

51-66-1

4'-Methoxyaceta...

Learn More
N/A Structure

124089-63-0

N/A

isopropylamine Structure

75-31-0

isopropylamine

~0%

N-Isopropylacetamide Structure

1118-69-0

N-Isopropylacetamide

ethyl 2-(2,4-dinitrophenyl)acetate Structure

68084-17-3

ethyl 2-(2,4-di...

Learn More
N/A Structure

124089-63-0

N/A

Diethylamine Structure

109-89-7

Diethylamine

~0%

N,N-Diethylacetamide Structure

685-91-6

N,N-Diethylacetamide

ethyl 2-(2,4-dinitrophenyl)acetate Structure

68084-17-3

ethyl 2-(2,4-di...

Learn More
N/A Structure

124089-63-0

N/A

1,2-Diaminopropane Structure

78-90-0

1,2-Diaminopropane

~0%

ethyl 2-(2,4-dinitrophenyl)acetate Structure

68084-17-3

ethyl 2-(2,4-di...

1-methyl-2-(methylcarbonylamino)ethylamine Structure

35397-63-8

1-methyl-2-(met...

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2-Amino-2-methyl-1-propanol Structure

124-68-5

2-Amino-2-methy...

N/A Structure

124089-63-0

N/A

~0%

2-amino-2-methylpropyl acetate Structure

25000-26-4

2-amino-2-methy...

ethyl 2-(2,4-dinitrophenyl)acetate Structure

68084-17-3

ethyl 2-(2,4-di...

Learn More
2,4-Dinitrochlorobenzene Structure

97-00-7

2,4-Dinitrochlo...

~%

ethyl 2-(2,4-dinitrophenyl)acetate Structure

68084-17-3

ethyl 2-(2,4-di...

Learn More
Ethanol Structure

64-17-5

Ethanol

N/A Structure

124089-63-0

N/A

~64%

ethyl 2-(2,4-dinitrophenyl)acetate Structure

68084-17-3

ethyl 2-(2,4-di...

ethyl acetate Structure

141-78-6

ethyl acetate

Learn More
Pyrrolidine Structure

123-75-1

Pyrrolidine

N/A Structure

124089-63-0

N/A

~98%

N-Acetylpyrrolidine Structure

4030-18-6

N-Acetylpyrrolidine

ethyl 2-(2,4-dinitrophenyl)acetate Structure

68084-17-3

ethyl 2-(2,4-di...

Learn More
N/A Structure

124089-63-0

N/A

Ethanethiol Structure

75-08-1

Ethanethiol

~75%

Ethyl thioacetate Structure

625-60-5

Ethyl thioacetate

ethyl 2-(2,4-dinitrophenyl)acetate Structure

68084-17-3

ethyl 2-(2,4-di...

Learn More
Ethyl 3-oxoglutarate Structure

105-50-0

Ethyl 3-oxoglutarate

~%

Propanoicacid, 3-(diethylamino)-3-oxo-, ethyl ester Structure

33567-70-3

Propanoicacid, ...

Learn More
N/A Structure

124089-63-0

N/A

Diethylamine Structure

109-89-7

Diethylamine

~99%

N,N-Diethylacetamide Structure

685-91-6

N,N-Diethylacetamide

ethyl 2-(2,4-dinitrophenyl)acetate Structure

68084-17-3

ethyl 2-(2,4-di...

Learn More

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