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

Research output: Contribution to journalArticlepeer-review

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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 languageEnglish
Pages (from-to)5008-5011
JournalTetrahedron Letters
Volume53
Issue number37
DOIs
Publication statusPublished - 2012

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