Synthesis of 1,3-Diaryltriazenes and Azo Dyes from Aryl Amines Using N-Nitrososulfonamides

New methods for the synthesis of 1,3-diaryltriazenes and azo dyes from aryl amines are reported. Both methods involve the for-mation of aryl diazonium intermediates via the transnitrosation of aryl amines with N-nitrososulfonamides. Each two-step transformation may be performed in one reaction vessel at room temperature with no precautions taken to exclude air or moisture. Several triazene and azo dye structures are reported here for the first time, demonstrating the utility of operating the two-step reaction sequence under mild conditions.

Automated summary

New methods for the synthesis of 1,3-diaryltriazenes and azo dyes from aryl amines are presented. These methods involve the formation of aryl diazonium intermediates through the transnitrosation of aryl amines with N-nitrososulfonamides. The reactions can be conducted in one vessel at room temperature without any precautionary measures to exclude air or moisture. The reported novel structures of triazenes and azo dyes demonstrate the effectiveness of the mild conditions for the two-step reaction sequence.