Studies on the acylation of 4-(2-aminoethylthio)-7-nitrobenzofurazan: the role of bases in promoting the formation of fluorescent S-acyl derivatives through S–N Smiles rearrangement

Daniele Castagnolo; Mafalda Pagano; Martina Bernardini; Maurizio Botta

doi:10.1016/j.tetlet.2012.07.033

Studies on the acylation of 4-(2-aminoethylthio)-7-nitrobenzofurazan: the role of bases in promoting the formation of fluorescent S-acyl derivatives through S–N Smiles rearrangement

Daniele Castagnolo, Mafalda Pagano, Martina Bernardini, Maurizio Botta

Northumbria University

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Abstract

The acylation of 4-(2-aminoethylthio)-7-nitrobenzofurazan has been investigated. Depending on the use of the base, a competitive Smiles rearrangement occurs during the acylation step leading to the formation of N-acyl and/or fluorescent S-acyl derivatives. The acylating agent also affects the ratio of N/S acylated isomers.

Original language	English
Pages (from-to)	5008-5011
Journal	Tetrahedron Letters
Volume	53
Issue number	37
DOIs	https://doi.org/10.1016/j.tetlet.2012.07.033
Publication status	Published - 2012

Keywords

S-N acylation
Smiles rearrangement
Fluorescent probe
Benzofurazan
Cysteamine

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10.1016/j.tetlet.2012.07.033

Castagnolo 10972 Revised manuscript - Tet Lett 2012Accepted author manuscript, 337 KB

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keywords = "S-N acylation, Smiles rearrangement, Fluorescent probe, Benzofurazan, Cysteamine",

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journal = "Tetrahedron Letters",

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Studies on the acylation of 4-(2-aminoethylthio)-7-nitrobenzofurazan: the role of bases in promoting the formation of fluorescent S-acyl derivatives through S–N Smiles rearrangement. / Castagnolo, Daniele; Pagano, Mafalda; Bernardini, Martina et al.
In: Tetrahedron Letters, Vol. 53, No. 37, 2012, p. 5008-5011.

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

TY - JOUR

T1 - Studies on the acylation of 4-(2-aminoethylthio)-7-nitrobenzofurazan: the role of bases in promoting the formation of fluorescent S-acyl derivatives through S–N Smiles rearrangement

AU - Castagnolo, Daniele

AU - Pagano, Mafalda

AU - Bernardini, Martina

AU - Botta, Maurizio

PY - 2012

Y1 - 2012

N2 - The acylation of 4-(2-aminoethylthio)-7-nitrobenzofurazan has been investigated. Depending on the use of the base, a competitive Smiles rearrangement occurs during the acylation step leading to the formation of N-acyl and/or fluorescent S-acyl derivatives. The acylating agent also affects the ratio of N/S acylated isomers.

AB - The acylation of 4-(2-aminoethylthio)-7-nitrobenzofurazan has been investigated. Depending on the use of the base, a competitive Smiles rearrangement occurs during the acylation step leading to the formation of N-acyl and/or fluorescent S-acyl derivatives. The acylating agent also affects the ratio of N/S acylated isomers.

KW - S-N acylation

KW - Smiles rearrangement

KW - Fluorescent probe

KW - Benzofurazan

KW - Cysteamine

U2 - 10.1016/j.tetlet.2012.07.033

DO - 10.1016/j.tetlet.2012.07.033

M3 - Article

SN - 0040-4039

VL - 53

SP - 5008

EP - 5011

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 37

ER -

Studies on the acylation of 4-(2-aminoethylthio)-7-nitrobenzofurazan: the role of bases in promoting the formation of fluorescent S-acyl derivatives through S–N Smiles rearrangement

Abstract

Keywords

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