Tert-Butyl Nitrite-initiated C-N Bond Cleavage of 1-Nitromethyl-N-aryltetrahydroisoquinolines: Synthesis of Furoxans with N-NO Skeleton

A series of furoxan derivatives with N-nitroso groups were synthesized in good yields by TBN initiated radical sp(3) C-N bond cleavage of 1-nitromethyl-N-aryltetrahydroisoquinolines. This reaction grafts the biologically important furoxan skeleton and N-nitroso group into on molecule, greatly improving the molecular complexity in one step transformation. The mechanistic study shows that this reaction is mediated by the in situ generated alpha-carbonyl nitrile oxide, which is afforded by TBN promoted C-N bond cleavage.

Automated summary

A series of furoxan derivatives with N-nitroso groups were efficiently synthesized by TBN-initiated radical sp(3) C-N bond cleavage of 1-nitromethyl-N-aryltetrahydroisoquinolines. This reaction introduces the biologically important furoxan skeleton and N-nitroso group into one molecule, significantly enhancing molecular complexity through a one-step transformation. Mechanistic studies reveal that this reaction is mediated by the in situ generated alpha-carbonyl nitrile oxide, which is formed via TBN-promoted C-N bond cleavage.