Benzene 1 2 diamine

All experiments were carried out in an atmosphere of dry argon and flasks were flame dried. Solvents were dried by usual methods (diphenyl ether, diethyl ether and THF over benzophenone ketyl, CHCl₃ and CH₂Cl₂ over P₄O₁₀, hexane over sodium-potassium alloy) and distilled. Chromatographic purification was carried out on silica gel 60 (0.15–0.3 mm, Macherey-Nagel GmbH & Co. KG, Düren, Germany). Sodium hydride (dry, 95%), trimethyl orthoformate, triethyl orthoformate, triethyl orthoacetate, trimethyl orthoacetate, 1,10-phenanthroline (4n), 1,10-phenanthrolin-5-amine (5l), 9H-carbazole, pyrrolidine, 10H-phenothiazine, Meldrum’s acid, benzene-1,2-diamine, 4-fluorobenzene-1,2-diamine, 4-chlorobenzene-1,2-diamine, 4-bromobenzene-1,2-diamine, 4-methylbenzene-1,2-diamine, 3,4-diaminobenzonitrile and 3,4-diaminobenzoic acid were purchased from Sigma–Aldrich (Poznan, Poland), and were used without further purification.

Reagents
like copper(II) chloride, copper(II)
acetate, DCFDA, calf thymus DNA (ct-DNA) sodium salt, benzene-1,2-diamine, N-chlorosuccinimide (NCS), 2-hydroxybenzaldehyde, p-toluenesulfonic acid (p-TsOH), bromine,
and 2-amino-2-(hydroxymethyl)propane-1,3-diol (TRIS) were obtained
from Sigma-Aldrich and Thermo Fisher. Solvents such as acetonitrile
(ACN), methanol (MeOH), ethanol (EtOH), ether, chloroform (CHCl₃), dimethyl sulfoxide (DMSO), ethyl acetate (EtOAc), dichloromethane
(DCM), acetic anhydride, and hexane were used at synthesis grade purity
and directly from commercial sources (Scharlab, Panreac and VWR).