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Synthesis 2023; 55(23): 3981-3990
DOI: 10.1055/a-2128-5335
DOI: 10.1055/a-2128-5335
paper
One-Pot Synthesis of Quinoxaline N-Oxides via Radical-Mediated Cyclization of Ketene N,S-Acetals
We gratefully acknowledge the financial support from the Science and Engineering Research Board (CRG/2019/000058), IoE Incentive grant (Scheme No. 6031) and JC Bose National Fellowship (JCB/2020/000023), New Delhi. The authors (G.K., S.R. and G.S.) are thankful to UGC & SERB, New Delhi for fellowships.
Abstract
A facile and efficient one-pot synthesis of bench-stable quinoxaline N-oxides has been realized using α-oxoketene N,S-acetals and tert-butyl nitrite (TBN) in open air via cascade annulation. The double functionalization of N,S-acetals proceeds through an unanticipated (Csp2)–H nitrosation by NO radical (generated in situ by TBN) and subsequent intramolecular N-arylation leading to quinoxaline, which undergoes oxidation to quinoxaline N-oxides harboring three variegated substituents on their framework. Notably, two new C–N bonds are formed with the same N-oxide nitrogen. This protocol features short reaction time, good functional group tolerance and mild conditions, and does not require the use of either catalyst or external additive.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-2128-5335.
- Supporting Information
- CIF File
Publikationsverlauf
Eingereicht: 09. Juni 2023
Angenommen nach Revision: 13. Juli 2023
Accepted Manuscript online:
13. Juli 2023
Artikel online veröffentlicht:
06. September 2023
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