0000000000001286
AUTHOR
Barbara Cosimelli
showing 7 related works from this author
Substituent effect on the redox potential of substituted (aryl)(2-nitrobenzo[ b ]thiophen-3-yl)amines
2001
Abstract The electronic effect of some meta- or para-substituents on the reduction of the title compounds has been investigated. The reversible reduction potential values of these compounds have been evaluated by cyclic voltammetry at a mercury electrode in 0.1 M tetraethylammoniumtetrafluoroborate, dimethylsulfoxide solutions. The substituent effect depends on both its nature and its position. The reduction potential values of the derivatives studied have been correlated with the Hammett substituent constants.
On the reactivity of 3-bromo-2-nitrobenzo[ b ]thiophene with nucleophiles: elucidation of the base-catalysed mechanism with rearrangement
2001
Abstract The reactivity of 3-bromo-2-nitrobenzo[b]thiophene (1) with several (anionic and neutral) nucleophiles has been examined. Only with neutral, weak nucleophiles (as anilines) 1 gives, in the presence of non-nucleophilic bases (triethylamine or potassium carbonate), together with the ‘expected’ 3-amino-2-nitrobenzo[b]thiophenes (3) also the ‘unexpected’ 2-amino-3-nitrobenzo[b]thiophenes (4). The composition of the final isomeric mixture depends on the base added (nature and quantity) and on the solvent used. The results demonstrate the relevance of base-catalysis and support a reaction pathway involving the formation of an anionic intermediate (B) which undergoes addition of a second …
Studies in organic mass spectrometry. Part 24† Electron ionization mass spectra of some aryl(2-nitrobenzo[b]thiophen-3-yl)amines
1999
The main fragmentation routes of eighteen title compounds and of three 5-chloro derivatives have been investigated with the aid of linked scan (B/E = constant) spectrometry, accurate mass measurements and deuterium labelling. Copyright © 1999 John Wiley & Sons, Ltd.
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 an…
2003
Abstract The title reaction, carried out in DMF in the presence of triethylamine or potassium carbonate, has furnished the ‘expected’ 3-amino-2-nitrobenzo[ b ]thiophenes 2 o together with the ‘unexpected’ 2-amino-3-nitrobenzo[ b ]thiophenes 3 o , thus recalling the situation observed with other weak nucleophiles in the presence of non-nucleophilic bases. The effects (electronic as well as steric) of the ortho -substituent (OH, NH 2 , OMe, Me, Et, F, Cl and Br) on the course of the reaction have been investigated, determining their influence on yields and product ratios ( 2 o / 3 o ). An analysis of 13 C NMR and MS spectra of 2 o and 3 o has been carried out. Ab initio computations on 2 o f …
ChemInform Abstract: On the Reactivity of Nitrosoimidazoles with Acids (the Cusmano-Ruccia Reaction): A Continuous Source of New Ring-into-Ring Inter…
2014
Abstract An extension of the ‘Cusmano–Ruccia’ reaction is reported. 6-(4-chlorophenyl)-3-methyl-5-nitrosoimidazo[2,1- b ]oxazole by the action of hydrochloric acid gives 3-(4-chlorobenzoyl)-5-methyl-1,2,4-oxadiazole ( 13 ); presumably via ammonium ion, CO 2 and methanol elimination. The relevance of the nature of the atom of the B -ring linked to C-2 of the imidazole for the occurrence of the ring-into-ring interconversion has been once more confirmed.
On the reactivity of nitrosoimidazoles with acids (the Cusmano–Ruccia reaction): a continuous source of new ring-into-ring interconversion
2014
Abstract An extension of the ‘Cusmano–Ruccia’ reaction is reported. 6-(4-chlorophenyl)-3-methyl-5-nitrosoimidazo[2,1- b ]oxazole by the action of hydrochloric acid gives 3-(4-chlorobenzoyl)-5-methyl-1,2,4-oxadiazole ( 13 ); presumably via ammonium ion, CO 2 and methanol elimination. The relevance of the nature of the atom of the B -ring linked to C-2 of the imidazole for the occurrence of the ring-into-ring interconversion has been once more confirmed.
The Boulton-Katritzky Reaction: A Kinetic Study of the Effect of 5-Nitrogen Substituents on the Rearrangement of Some (Z)-Phenylhydrazones of 3-Benzo…
2014
The kinetics of the ring-into-ring conversion of some new (Z)-phenylhydrazones of 3-benzoyl-1,2,4-oxadiazole containing different nitrogen-substituents at C-5 (3b–d; X = NHMe, NMe2, and NHCOMe) into the relevant triazoles 4b–d have been examined in a wide range of pS+ (0.1–11.9) in 1:1 (v/v) dioxane/water solution. The obtained results have been compared with previous data concerning the (Z)-phenylhydrazone of 5-amino-3-benzoyl-1,2,4-oxadiazole (3a; X = NH2). All of the studied (Z)-phenylhydrazones rearrange through three different pathways (specific acid-catalysed, uncatalysed and general base-catalysed). The different effects of the substituents on the course of the rearrangement in the t…