Preparation of sulfonamides from N-silylamines

Rajasekhar Reddy Naredla; Douglas A. Klumpp

doi:10.1016/j.tetlet.2013.08.034

Preparation of sulfonamides from N-silylamines

Rajasekhar Reddy Naredla, Douglas A. Klumpp

Research output: Contribution to journal › Article › peer-review

9 Scopus citations

Abstract

Sulfonamides have been prepared in high yields by the reactions of N-silylamines with sulfonyl chlorides and fluorides. In a competition experiment, the sulfonyl chlorides were found to be far more reactive than sulfonyl fluorides. The chemistry may be used to prepare aliphatic, aromatic, tertiary, secondary, and primary sulfonamides. It may also be done in the absence of solvent and the byproduct trimethylsilyl chloride recovered in good yield. Primary sulfonamides were synthesized from the sulfonyl chloride with aminotriphenyl silane (Ph₃SiNH₂), a conversion demonstrated with the synthesis of the carbonic anhydrase inhibitor, acetazolamide.

Original language	English (US)
Pages (from-to)	5945-5947
Number of pages	3
Journal	Tetrahedron Letters
Volume	54
Issue number	45
DOIs	https://doi.org/10.1016/j.tetlet.2013.08.034
State	Published - Nov 6 2013
Externally published	Yes

Bibliographical note

Funding Information:
We gratefully acknowledge the support of the NIH-National Institute of General Medical Sciences (GM085736-01A1) and the Northern Illinois University for Great Journeys Fellowship (R.R.N.). This manuscript is dedicated to Rachel A. Klumpp on the occasion of her tenth birthday.

Keywords

N-Silylamine
Substitution
Sulfonamides
Sulfonyl transfer

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10.1016/j.tetlet.2013.08.034

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title = "Preparation of sulfonamides from N-silylamines",

abstract = "Sulfonamides have been prepared in high yields by the reactions of N-silylamines with sulfonyl chlorides and fluorides. In a competition experiment, the sulfonyl chlorides were found to be far more reactive than sulfonyl fluorides. The chemistry may be used to prepare aliphatic, aromatic, tertiary, secondary, and primary sulfonamides. It may also be done in the absence of solvent and the byproduct trimethylsilyl chloride recovered in good yield. Primary sulfonamides were synthesized from the sulfonyl chloride with aminotriphenyl silane (Ph3SiNH2), a conversion demonstrated with the synthesis of the carbonic anhydrase inhibitor, acetazolamide.",

keywords = "N-Silylamine, Substitution, Sulfonamides, Sulfonyl transfer",

author = "Naredla, {Rajasekhar Reddy} and Klumpp, {Douglas A.}",

note = "Funding Information: We gratefully acknowledge the support of the NIH-National Institute of General Medical Sciences (GM085736-01A1) and the Northern Illinois University for Great Journeys Fellowship (R.R.N.). This manuscript is dedicated to Rachel A. Klumpp on the occasion of her tenth birthday. ",

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T1 - Preparation of sulfonamides from N-silylamines

AU - Naredla, Rajasekhar Reddy

AU - Klumpp, Douglas A.

N1 - Funding Information: We gratefully acknowledge the support of the NIH-National Institute of General Medical Sciences (GM085736-01A1) and the Northern Illinois University for Great Journeys Fellowship (R.R.N.). This manuscript is dedicated to Rachel A. Klumpp on the occasion of her tenth birthday.

PY - 2013/11/6

Y1 - 2013/11/6

N2 - Sulfonamides have been prepared in high yields by the reactions of N-silylamines with sulfonyl chlorides and fluorides. In a competition experiment, the sulfonyl chlorides were found to be far more reactive than sulfonyl fluorides. The chemistry may be used to prepare aliphatic, aromatic, tertiary, secondary, and primary sulfonamides. It may also be done in the absence of solvent and the byproduct trimethylsilyl chloride recovered in good yield. Primary sulfonamides were synthesized from the sulfonyl chloride with aminotriphenyl silane (Ph3SiNH2), a conversion demonstrated with the synthesis of the carbonic anhydrase inhibitor, acetazolamide.

AB - Sulfonamides have been prepared in high yields by the reactions of N-silylamines with sulfonyl chlorides and fluorides. In a competition experiment, the sulfonyl chlorides were found to be far more reactive than sulfonyl fluorides. The chemistry may be used to prepare aliphatic, aromatic, tertiary, secondary, and primary sulfonamides. It may also be done in the absence of solvent and the byproduct trimethylsilyl chloride recovered in good yield. Primary sulfonamides were synthesized from the sulfonyl chloride with aminotriphenyl silane (Ph3SiNH2), a conversion demonstrated with the synthesis of the carbonic anhydrase inhibitor, acetazolamide.

KW - N-Silylamine

KW - Substitution

KW - Sulfonamides

KW - Sulfonyl transfer

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JO - Tetrahedron Letters

JF - Tetrahedron Letters

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ER -

Preparation of sulfonamides from N-silylamines

Abstract

Bibliographical note

Keywords

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