Thioacids Mediated Selective and Mild N-Acylation of Amines

SM Mali, RD Bhaisare, HN Gopi

Index: Taylor, James E.; Jones, Matthew D.; Williams, Jonathan M. J.; Bull, Steven D. Journal of Organic Chemistry, 2012 , vol. 77, # 6 p. 2808 - 2818

Full Text: HTML

Citation Number: 17

Abstract

... E-mail: hn.gopi@iiserpune.ac.in ... acids, thioacids have recently gained momentum due to their unique reactivity and selectivity in the amide bond formations.(32-34) Williams et al ... 1493, 1468, 1435, 1319, 1260, 755, 696; 1 H NMR (400 MHz; CDCl 3 ) δ 7.70 (br, 1H), 7.5 (d, 2H, J ...

 Related Synthetic Route
4-AMINOPYRIDINE Structure

504-24-5

4-AMINOPYRIDINE

N5-acetyl-DBN*BPh4 Structure

1363906-80-2

N5-acetyl-DBN*BPh4

~80%

N-(PYRIDIN-4-YL)ACETAMIDE Structure

5221-42-1

N-(PYRIDIN-4-YL...

morpholine Structure

110-91-8

morpholine

N5-acetyl-DBN*BPh4 Structure

1363906-80-2

N5-acetyl-DBN*BPh4

~97%

N-Acetylmorpholine Structure

1696-20-4

N-Acetylmorpholine

BTS Structure

1576-37-0

BTS

N5-acetyl-DBN*BPh4 Structure

1363906-80-2

N5-acetyl-DBN*BPh4

~63%

N-benzyl-N-(4-methylphenyl)sulfonylacetamide Structure

121618-47-1

N-benzyl-N-(4-m...

4-picolinylamine Structure

3731-53-1

4-picolinylamine

N5-acetyl-DBN*BPh4 Structure

1363906-80-2

N5-acetyl-DBN*BPh4

~78%

Acetamide,N-(4-pyridinylmethyl)- Structure

23974-15-4

Acetamide,N-(4-...

N5-acetyl-DBN*BPh4 Structure

1363906-80-2

N5-acetyl-DBN*BPh4

Dibenzylamine Structure

103-49-1

Dibenzylamine

~70%

Acetamide,N,N-bis(phenylmethyl)- Structure

10479-30-8

Acetamide,N,N-b...

Piperazine Structure

110-85-0

Piperazine

N5-acetyl-DBN*BPh4 Structure

1363906-80-2

N5-acetyl-DBN*BPh4

~99%

1-Acetylpiperazine Structure

13889-98-0

1-Acetylpiperazine

Benzenesulfonamide Structure

98-10-2

Benzenesulfonamide

N5-acetyl-DBN*BPh4 Structure

1363906-80-2

N5-acetyl-DBN*BPh4

~83%

N-(benzenesulfonyl)acetamide Structure

5661-14-3

N-(benzenesulfo...

1-ethyl-carboxyl-2,3,4,6,7,8-hexahydropyrrolo[1,2-a]pyrimidinium tetraphenylborate Structure

1363906-94-8

1-ethyl-carboxy...

Benzylamine Structure

100-46-9

Benzylamine

~80%

Carbamic acid,N-(phenylmethyl)-, ethyl ester Structure

2621-78-5

Carbamic acid,N...

N5-acetyl-DBN*BPh4 Structure

1363906-80-2

N5-acetyl-DBN*BPh4

Structure

74497-02-2

~87%

Acetanilide Structure

103-84-4

Acetanilide

Methanesulfonamide Structure

3144-09-0

Methanesulfonamide

N5-acetyl-DBN*BPh4 Structure

1363906-80-2

N5-acetyl-DBN*BPh4

~98%

N-methylsulfonylacetamide Structure

81005-29-0

N-methylsulfony...

N5-acetyl-DBN*BPh4 Structure

1363906-80-2

N5-acetyl-DBN*BPh4

p-Anisidine Structure

104-94-9

p-Anisidine

~74%

4'-Methoxyacetanilide Structure

51-66-1

4'-Methoxyaceta...

Methyl L-phenylalaninate Structure

2577-90-4

Methyl L-phenyl...

N5-acetyl-DBN*BPh4 Structure

1363906-80-2

N5-acetyl-DBN*BPh4

~99%

Methyl N-acetyl-L-phenylalaninate Structure

3618-96-0

Methyl N-acetyl...

N5-acetyl-DBN*BPh4 Structure

1363906-80-2

N5-acetyl-DBN*BPh4

2-Phenylethanamine Structure

64-04-0

2-Phenylethanamine

~98%

N-(2-Phenylethyl)acetamide Structure

877-95-2

N-(2-Phenylethy...

N5-acetyl-DBN*BPh4 Structure

1363906-80-2

N5-acetyl-DBN*BPh4

Benzylamine Structure

100-46-9

Benzylamine

~97%

n-benzylacetamide Structure

588-46-5

n-benzylacetamide

1,3-Benzodioxol-5-Ylmethylamine Structure

2620-50-0

1,3-Benzodioxol...

N5-acetyl-DBN*BPh4 Structure

1363906-80-2

N5-acetyl-DBN*BPh4

~67%

N-(benzo[1,3]dioxol-5-ylmethyl)acetamide Structure

59682-83-6

N-(benzo[1,3]di...

N5-acetyl-DBN*BPh4 Structure

1363906-80-2

N5-acetyl-DBN*BPh4

tert-Butylamine Structure

75-64-9

tert-Butylamine

~76%

Acetamide,N-(1,1-dimethylethyl)- Structure

762-84-5

Acetamide,N-(1,...

Pyrrolidine Structure

123-75-1

Pyrrolidine

N5-acetyl-DBN*BPh4 Structure

1363906-80-2

N5-acetyl-DBN*BPh4

~86%

N-Acetylpyrrolidine Structure

4030-18-6

N-Acetylpyrrolidine

N5-acetyl-DBN*BPh4 Structure

1363906-80-2

N5-acetyl-DBN*BPh4

Benzylisopropylamine Structure

102-97-6

Benzylisopropylamine

~56%

N-benzyl-N-propan-2-ylacetamide Structure

55578-20-6

N-benzyl-N-prop...

N5-acetyl-DBN*BPh4 Structure

1363906-80-2

N5-acetyl-DBN*BPh4

p-Toluidine Structure

106-49-0

p-Toluidine

~91%

4'-Methylacetanilide Structure

103-89-9

4'-Methylacetanilide

N5-acetyl-DBN*BPh4 Structure

1363906-80-2

N5-acetyl-DBN*BPh4

4-Toluenesulfonamide Structure

70-55-3

4-Toluenesulfonamide

~77%

N-(4-Methylphenyl)sulfonylacetamide Structure

1888-33-1

N-(4-Methylphen...


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