Journal
CHEMISTRY-AN ASIAN JOURNAL
Volume -, Issue -, Pages -Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/asia.202201265
Keywords
tert-Butyl nitrite; C-N bond cleavage; Furoxans; 1-Nitromethyl-N-aryltetrahydroisoquinolines; N-Nitrosamines
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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.
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.
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