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. (C) 2012 Elsevier Ltd. All rights reserved.
Castagnolo, D., Pagano, M., Bernardini, M., Botta, M. (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), 5008-5011 [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
Castagnolo, Daniele;Pagano, Mafalda;Bernardini, Martina;Botta, Maurizio
2012-01-01
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. (C) 2012 Elsevier Ltd. All rights reserved.
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https://hdl.handle.net/11365/49134
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