Synthesis of Fused Diaziridine Derivatives from Cyclic Secondary Amines by Utilizing N-Bromosulfonamides as an Aminating Reagent

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 compounds

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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