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 α-carbonyl nitrile oxide, which is afforded by TBN promoted C-N bond cleavage.