Tert‐Butyl Nitrite‐initiated C−N Bond Cleavage of 1‐Nitromethyl‐N‐aryltetrahydroisoquinolines: Synthesis of Furoxans with N−NO Skeleton
摘要:
AbstractA series of furoxan derivatives with N‐nitroso groups were synthesized in good yields by TBN initiated radical sp3 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.
The direct α-C(sp<sup>3</sup>)–H functionalisation of N-aryl tetrahydroisoquinolines via an iron-catalysed aerobic nitro-Mannich reaction and continuous flow processing
作者:Martin Brzozowski、Jose A. Forni、G. Paul Savage、Anastasios Polyzos
DOI:10.1039/c4cc07913b
日期:——
An efficient nitro-Mannich type direct α-C(sp3)–H functionalisation of N-aryl-1,2,3,4-tetrahydroisoquinolines catalysed by simple iron salts in combination with O2 as the terminal oxidant is described.
organic electron donor (OED), the reduction of “push–pull” C–C single bond and reductivedecyanation of tetrahydroisoquinolines were realized. These reactions exhibited higher reaction efficiency and better functional group tolerance compared with those of metallic reductants, and the mechanistic study indicated that a radicalintermediate was involved in the reduction of the C–C single bond, which provides