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Abstract A two-stage method for the preparation of 2-(3-carboxymethylindazol-1-yl)anilines using the N-arylation reaction of 3-carboxymethylindazoles with o-nitrohaloarenes and subsequent reduction of nitro-containing intermediates with tin(II) chloride was developed. The experimental results showed that the use of the synthesized compounds as fluorophores in the visible region of the spectrum is promising.

An efficient one-pot method was developed for the synthesis of 2-(1,2,4-oxadiazol-5-yl)anilines via the reaction of amidoximes with isatoic anhydrides in a NaOH–DMSO medium at ambient temperature. The method allows to obtain structurally diverse substituted anilines bearing the 1,2,4-oxadiazole motif in moderate to excellent yields without the utilization of protective groups. The reaction scope includes aryl, hetaryl, and cycloalkyl amidoxime and isatoic anhydrides with different substituents in the aromatic ring as well as at the amide N atom. Structures of two anilines were studied by single crystal X-ray diffraction method and intramolecular hydrogen bonding between N atom of oxadiazole moiety and NH2 group was revealed.