6533b830fe1ef96bd1297a6a
RESEARCH PRODUCT
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
Raffaella SpisaniFederica VegnaLiliana LamartinaBarbara CosimelliCamilla Zaira LanzaDomenico Spinellisubject
Steric effectsChemistryOrganic ChemistrySubstituentCarbon-13 NMRBiochemistryMedicinal chemistryPotassium carbonatechemistry.chemical_compoundNucleophileNucleophilic aromatic substitutionDrug DiscoveryThiopheneTriethylaminedescription
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 , 2 o i , 3 o f and 3 o i at DFT level have furnished informations on their geometry and stability in the gas phase, thus allowing to assign a role to their stability on the course of the reaction as well as on some EI-MS results.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2003-09-01 | Tetrahedron |