A Barton nitrite ester-type remote functionalization and cyclization of N-nitrosobenzamides
ORGANIC CHEMISTRY FRONTIERS(2023)
摘要
An efficient Barton nitrite ester-type cyclization reaction of N-ethyl-N-nitrosobenzamides to synthesize benzo[d][1,2]oxazin-1-ones was established. The reaction proceeds via the homogeneous cleavage of N-N bonds to neutrally generate a nitrogen-centered radical with an intramolecular H-atom transfer (HAT) occurring in a highly efficient way. Interestingly, the N-nitrosobenzamides are converted to the corresponding & gamma;-hydroxy oximes in the reaction first, and then a nucleophilic attack occurs to afford the desired benzo[d][1,2]oxazin-1-ones efficiently.
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关键词
ester-type,n-nitrosobenzamides
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