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 and Botta, Maurizio (2012) 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. Tetrahedron Letters, 53 (37). pp. 5008-5011. ISSN 0040-4039

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Official URL: http://dx.doi.org/10.1016/j.tetlet.2012.07.033

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.

Item Type: Article
Uncontrolled Keywords: S-N acylation; Smiles rearrangement; Fluorescent probe; Benzofurazan; Cysteamine
Subjects: F100 Chemistry
Department: Faculties > Health and Life Sciences > School of Life Sciences > Applied Sciences
Depositing User: Linda Barlow
Date Deposited: 08 Jan 2013 13:23
Last Modified: 09 May 2017 05:14
URI: http://nrl.northumbria.ac.uk/id/eprint/10972

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