On the reaction between 3-bromo-2-nitrobenzo[b]thiophene and some amines: a novel aromatic nucleophilic substitution with rearrangement

doi:10.1039/P19950001243

Paper

On the reaction between 3-bromo-2-nitrobenzo[b]thiophene and some amines: a novel aromatic nucleophilic substitution with rearrangement

Published Jan 1, 1995 · F. Guerrera, L. Salerno, L. Lamartina

Journal of The Chemical Society-perkin Transactions 1

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Abstract

3-Bromo-2-nitrobenzo[b]thiophene reacted with some amines in N,N-dimethylformamide giving, together with the expected N-substituted 3-amino-2-nitrobenzo[b]thiophenes 3 deriving from aromatic nucleophilic substitution, their isomers 4, whose unexpected structure of N-substituted 2-amino-3-nitrobenzo[b]thiophenes has been determined by means of spectroscopic techniques. As 2-bromo-3-nitrobenzo[b]thiophene gave tars with nucleophiles, the observed reaction could be of use for the synthesis of 4. Some hypotheses on the mechanism of formation of 3 and 4 are suggested.

Study Snapshot

This study demonstrates a novel aromatic nucleophilic substitution with rearrangement reaction between 3-bromo-2-nitrobenzo[b]thiophene and amines, leading to unexpected isomers and potential applications in synthesis of 4-amino-3-nitrobenzo[b]thiophenes

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

On the reaction between 3-bromo-2-nitrobenzo[b]thiophene and some amines: a novel aromatic nucleophilic substitution with rearrangement

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