Aziridines via Triazolines

The rate at which nitrogen is lost from triazolines is very dependent upon substituents. For example, A-cyanotriazolines decompose at temperatures between 0°C and 35 °C, 

Some applications of the triazoline route to aziridines from alkenes and azides are described below. 

1 Combinations of Nucleophilic Alkenes and Electron Deficient Azides 

A short synthetic sequence to a benzazocenone 46, a potential building block for mito-mycenoids and related antitumour compounds, makes use of an intramolecular addition 

The ring opening of epoxides by inorganic azides is the initial step of a general synthetic route to aziridines. Because enantiopure epoxides are readily available by Sharpless epoxidation and other methods, their ring opening by azide ions provides one of the best approaches to the synthesis of enantiopure aziridines. The stereochemistry of the aziridines can be reliably predicted on the basis of the mechanisms of the steps involved. 

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