Synthesis of potential bioactive polysubstituted naphthalene derivatives

Naphthols are electron-rich naphthalene derivatives with a hydroxyl group attached to one of the carbon atoms. α- and β-naphthol are two structural isomers and are very important starting materials for the synthesis of complex organic molecules. Naphthols can be easily converted into many new compounds through reactions such as alkylation, arylation, cyclization, amination, halogenation, etc. The aim of this study is to synthesize potentially bioactive naphthol derivatives and to obtain highly reactive bromonaphthols. For this purpose, the first step involved the synthesis of both nitrous and brominated derivatives of naphthol and their reactions with simple nitrating and brominating agents, yielding compounds 3, 4, 5, 6, 7, 8, 9, and 10 in good purity. In the second step, we used the bromonaphthol compounds obtained to attach the nitro group to the same ring as the bromine atom using conventional nitrating agents. As a result of these studies, nitronaphthols, in which the nitro group was replaced by bromine atoms, or oxidation products were obtained. Compounds 8, 10, and 11 were obtained as a result of these reactions.