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 1995 · F. Guerrera, L. Salerno, L. Lamartina

Journal of The Chemical Society-perkin Transactions 1

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19

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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.

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Paper

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

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References

Chemistry of thienopyridines. XXXVI: Further studies on nitration in the thieno[2,3-b]- and thieno[3,2-b]pyridine systems

Nitric and sulfuric acids nitrate thieno[3,2-b]pyridine 4-oxide, producing 1,7-dinitrothieno[3,2-b]pyridine 4-oxide, and 6-carbamoyl-5-nitrothieno[2,3-b]pyridine, respectively

A STUDY OF THE SUBSTITUTION REACTIONS OF BENZO[b]THIOPHENE AND ITS DERIVATIVES

New benzo[b]thiophenes were prepared and directional influences in the thiophene portion of the nucleus were confirmed.

Citations

The Boulton–Katritzky Reaction: A Kinetic Study of the Effect of 5‐Nitrogen Substituents on the Rearrangement of Some (Z)‐Phenylhydrazones of 3‐Benzoyl‐1,2,4‐oxadiazoles

Different nitrogen-substituents at C-5 affect the kinetics of ring-into-ring conversion of 3-benzoyl-1,2,4-oxadiazole (Z)-phenylhydrazones into triazoles, with specific acid-catalyzed, uncat

Uncommon 1,2-Migration of a Nitro Group Within a β-Nitrostyryl Moiety: Synthetic Scope and Mechanistic Details

The unusual 1,2-migration of a nitro group within a -nitrostyryl moiety allows for the controlled synthesis of two series of isomeric isoxazoline N-oxides and a new pyrazolylisoxazole.

A Novel Approach to the Evaluation of the Importance of Steric and Electronic Effects in SNAr Reactions: A Computational, Thermodynamic and 1H and 13C NMR Study of "Meisenheimer-Type" Adducts in the Benzo[b]thiophene Series

The formation of "Meisenheimer-type" adducts in benzo[b]thiophene series is thermodynamically more favorably due to electronic effects, while gem-dimethoxy adducts show steric effects predominating.

Substituent effect on the electrochemical behaviour of some ortho-substituted (aryl)(2-nitrobenzo[ b ]thiophen-3-yl)amines. A combined experimental and computational study

The ortho-substituent in (aryl)(2-nitrobenzo[b]thiophen-3-yl)amines affects their reduction potential values mainly through electronic effects, with the 2′-hydroxy substituent assisting proton transfer through hydrogen bonds.

On the reaction of 3-bromo-2-nitrobenzo[b]thiophene with some ortho-substituted anilines: an analysis of the products of reaction and of their NMR and MS properties

The reaction of 3-bromo-2-nitrobenzo[b]thiophene with ortho-substituted anilines produces expected and unexpected products, with the ortho-substituent's electronic and steric effects influencing yields and product ratios.