Issue 18, 2023

A Barton nitrite ester-type remote functionalization and cyclization of N-nitrosobenzamides

Abstract

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 γ-hydroxy oximes in the reaction first, and then a nucleophilic attack occurs to afford the desired benzo[d][1,2]oxazin-1-ones efficiently.

Graphical abstract: A Barton nitrite ester-type remote functionalization and cyclization of N-nitrosobenzamides

Supplementary files

Article information

Article type
Research Article
Submitted
16 Jun 2023
Accepted
21 Jul 2023
First published
24 Jul 2023

Org. Chem. Front., 2023,10, 4559-4564

A Barton nitrite ester-type remote functionalization and cyclization of N-nitrosobenzamides

T. Huang, P. Yuan, K. Dong, Y. Zong, C. Liu, R. Wang, X. Jin and Q. Liu, Org. Chem. Front., 2023, 10, 4559 DOI: 10.1039/D3QO00896G

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