A new azo compound was prepared via the azo coupling reaction between 4-(ethoxycarbonyl)-3-methyl-1H-pyrazole-5-diazonium chloride and 8-hydroxyquinoline (oxine). The ester functional group of the obtained compound was hydrolyzed and thus a new chemical structure with a carboxylic functional group resulted. The structures of the new compounds were fully characterized by: UV–Vis, FT-IR, 1D and 2D NMR spectroscopy, and HRMS spectrometry.
Tertiary butyl hypochlorite reacts with
2-nitroaniline, 4-nitroaniline, N-methyl-4-nitroaniline, and
NN-dimethyl-4-nitroaniline to form excellent yields of nuclear-chlorinated
derivatives. Direct oxidation, to form azo compounds, is also observed with
4-nitroaniline and the yield of azo compound increases at higher temperatures.
Demethylation also occurs when N-methyl-4-nitroaniline and
NN-dimethyl-4-nitro-aniline are used.
A new and convenient method for preparing 2,5-dimethylpyrrole, by the interaction of acetonylacetone and ammonium carbonate, is described. It may be identified by the formation of three solid derivatives: (a) the azo compound; (b) the mono-2,4-dinitrophenylhydrazone of acetonylacetone; and (c) its condensation product with acetone.
A practical and highly efficient azo-compound-mediated/ promoted radical cyanoalkylation of activated alkenes by copper catalysis was developed, which allowed for general synthesis of oxindoles bearing various nitrile moieties, especially the rarely reported 3° nitrile moiety via cascade radical addition/C(sp2)–H cyclization. This protocol demonstrates that DIAD served for a new promoter instead of usual Ag salts or bases in the C(sp3)–H functionalization of acetonitrile for the first time. The use of readily available AIBN and beyond as the radical sources, and inexpensive copper as the catalyst, as well as the simplicity of operation and handling, make this protocol an attractive access to therapeutically important cyano-substituted oxindoles.
5-((8-Hydroxyquinolin-5-yl)diazenyl)-3-methyl-1H-pyrazole-4-carboxylic Acid