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How is aziridine formed through nucleophilic ring closure?
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heterocyclic compound
There are many different sulfur-containing heterocycles. One of the best known is thiophene, C4H4S, derivatives of which occur as plant pigments and as other natural products such as biotin.
Aziridine is a three-membered heterocyclic compound that can be prepared through nucleophilic ring closure. Specifically, it is formed by heating -aminoethyl hydrogen sulfate in the presence of a base.1
This process involves an intramolecular reaction where the nitrogen atom acts as a nucleophile, displacing the sulfate group to close the ring. A similar mechanism occurs in the pharmacological action of nitrogen mustards, such as mechlorethamine. In these cases, the molecule undergoes internal cyclization to produce an intermediate aziridinium ion, which is the biologically active species capable of attacking DNA in rapidly proliferating cancer cells.1