Studio di intermedi e prodotti di sostituzione in reazioni di accoppiamento C-C fra derivati benzofurazanici e nucleofili aromatici ed eteroaromatici

This work is based on the study of electrophile/nucleophile combinations in aromatic substitution reactions. In particular, C-C coupling reactions were carried out using 10-π heteroaromatic systems like benzofuroxans or benzofurazans and neutral aromatic nucleophiles such as 1,3,5-triamminobenzene-, 1,3,5- trihydroxybenzene- or 2-aminothiazole- derivatives. The presence on electrophilic reagents of good leaving groups such as the chlorine atom allowed to obtain substitution products, with a scaffold bearing both an electron-donor and an electron-acceptor moiety. This kind of products can be of great interest in applicative fields, for example in the biological field and as materials for the conversion of energy. Moreover, by combining electrophiles such as 4,6-dinitrobenzofuroxan, 4,6-dinitrobenzofurazan and 4,6-dinitrotetrazolopyridine with 1,3,5-trihydroxybenzene- or 2-aminothiazole- derivatives, new Meisenheimer intermediates have been identified and characterized by NMR experiment at variable temperature.