Organic letters

Aryl (sulfonyl) amino Group: A convenient and stable yet activated modification of amino group for its intramolecular displacement

Y Kato, DH Yen, Y Fukudome, T Hata, H Urabe

Index: Kato, Yuzo; Yen, Dinh Hoang; Fukudome, Yasuhiro; Hata, Takeshi; Urabe, Hirokazu Organic Letters, 2010 , vol. 12, # 18 p. 4137 - 4139

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Citation Number: 8

Abstract

Aryl (sulfonyl) amino groups, readily derived from sulfonyl-or arylamines by standard methods as well as the recently introduced methods of sulfonylation and arylation, proved to be good leaving groups in intramolecular substitution reactions by various nitrogen, oxygen, and carbon nucleophiles.

 Related Synthetic Route
N-(o-nitrophenyl)-[5,5-di(benzenesulfonyl)pentyl]-p-toluenesulfonamide Structure

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N-(o-nitropheny...

~83%

[1-(benzenesulfonyl)cyclopentyl]sulfonylbenzene Structure

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[1-(benzenesulf...

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1-[(4-Methylphenyl)sulfonyl]pyrrolidine Structure

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N-(p-methoxyphe...

~99%

1-[(4-Methylphenyl)sulfonyl]pyrrolidine Structure

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1-[(4-Methylphe...

N/A Structure

1243273-66-6

N/A

~90%

1-[(4-Methylphenyl)sulfonyl]pyrrolidine Structure

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1-[(4-Methylphe...

N/A Structure

1243273-47-3

N/A

~69%

1-[(4-Methylphenyl)sulfonyl]pyrrolidine Structure

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1-[(4-Methylphe...

N-(p-methoxyphenyl)-N,N'-di(p-toluenesulfonyl)-1,4-butanediamine Structure

1243273-48-4

N-(p-methoxyphe...

~74%

1-[(4-Methylphenyl)sulfonyl]pyrrolidine Structure

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1-[(4-Methylphe...

N/A Structure

1243273-67-7

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~99%

1-[(4-Methylphenyl)sulfonyl]pyrrolidine Structure

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4-methyl-N-(4-((4-methylphenyl)sulfonamido)butyl)-N-(4-nitrophenyl)benzenesulfonamide Structure

1243273-69-9

4-methyl-N-(4-(...

~97%

1-[(4-Methylphenyl)sulfonyl]pyrrolidine Structure

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1-[(4-Methylphe...

4-methyl-N-(4-((4-methylphenyl)sulfonamido)butyl)-N-(4-(trifluoromethyl)phenyl)benzenesulfonamide Structure

1243273-70-2

4-methyl-N-(4-(...

~99%

1-[(4-Methylphenyl)sulfonyl]pyrrolidine Structure

6435-78-5

1-[(4-Methylphe...

N/A Structure

1243273-68-8

N/A

~99%

1-[(4-Methylphenyl)sulfonyl]pyrrolidine Structure

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1-[(4-Methylphe...

Benzenesulfonamide,4-methyl-N-(2-nitrophenyl)- Structure

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Benzenesulfonam...

N-(4-methoxyphenyl)-4-methyl-N-(5-((4-methylphenyl)sulfonamido)pentyl)benzenesulfonamide Structure

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1-(p-Tolylsulfonyl)piperidine Structure

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1-(p-Tolylsulfo...

4-methyl-N-(5-((4-methylphenyl)sulfonamido)pentyl)-N-(4-(trifluoromethyl)phenyl)benzenesulfonamide Structure

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4-methyl-N-(5-(...

~98%

1-(p-Tolylsulfonyl)piperidine Structure

4703-22-4

1-(p-Tolylsulfo...

4-methyl-N-(5-((4-methylphenyl)sulfonamido)pentyl)-N-(2-nitrophenyl)benzenesulfonamide Structure

1243273-72-4

4-methyl-N-(5-(...

~64%

1-(p-Tolylsulfonyl)piperidine Structure

4703-22-4

1-(p-Tolylsulfo...

Benzenesulfonamide,4-methyl-N-(2-nitrophenyl)- Structure

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Benzenesulfonam...

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~99%

1-[(4-Methylphenyl)sulfonyl]pyrrolidine Structure

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1-[(4-Methylphe...

Benzenesulfonamide,4-methyl-N-(2-nitrophenyl)- Structure

6380-13-8

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4-methyl-N-(5-((4-methylphenyl)sulfonamido)pentyl)-N-(2-nitrophenyl)benzenesulfonamide Structure

1243273-72-4

4-methyl-N-(5-(...

~64%

1-(p-Tolylsulfonyl)piperidine Structure

4703-22-4

1-(p-Tolylsulfo...

Benzenesulfonamide,4-methyl-N-(2-nitrophenyl)- Structure

6380-13-8

Benzenesulfonam...

N/A Structure

1243273-31-5

N/A

~88%

Pyrrolidine, 1-[(2-nitrophenyl)sulfonyl]- Structure

327069-81-8

Pyrrolidine, 1-...


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