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Synthesis 2021; 53(17): 3101-3109
DOI: 10.1055/a-1468-8275
DOI: 10.1055/a-1468-8275
special topic
Bond Activation – in Honor of Prof. Shinji Murai
Synthesis of Fused Diaziridine Derivatives from Cyclic Secondary Amines by Utilizing N-Bromosulfonamides as an Aminating Reagent
Authors
This work was supported by Japan Society for the Promotion of Science (JSPS) KAKENHI Grant Numbers JP19H02716 (S.M.) and JP20K05511 (K.K.).
In memory of Prof. Dr. Kilian Muñiz (1970−2020)
Abstract
The synthesis of a series of fused diaziridines, which are difficult to access by existing methods, was achieved by the reaction of cyclic secondary amines with p-toluenesulfonamide in the presence of N-bromosuccinimide (NBS) and a suitable base. This oxidation system enables the efficient in situ formation of the key intermediates, which are N-bromoamines (a precursor of cyclic imines) and N-bromosulfonamides. In addition, an alternative method using N-bromo-N-sodio-p-toluenesulfonamide (bromamine-T) in the presence of a catalytic amount of CF3CO2H for the synthesis of fused diaziridines is also reported.
Key words
cyclic secondary amines - cyclization - diaziridines - N-bromosulfonamides - nitrogen-containing heterocyclic compoundsSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-1468-8275.
- Supporting Information (PDF)
Publication History
Received: 12 March 2021
Accepted after revision: 29 March 2021
Accepted Manuscript online:
29 March 2021
Article published online:
20 April 2021
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