Azetidine


Azetidine is a saturated heterocyclic organic compound containing three carbon atoms and one nitrogen atom. It is a liquid at room temperature with a strong odor of ammonia and is strongly basic compared to most secondary amines.

Synthesis and occurrence

Azetidines can be prepared by reduction of azetidinones with lithium aluminium hydride. Even more effective is a mixture of lithium aluminium hydride and aluminium trichloride, a source of "AlClH2" and "AlCl2H". Azetidine can also be produced by a multistep route from 3-amino-1-propanol.
Azetidine and its derivatives are relatively rare structural motifs in natural products. They are a component of mugineic acids and penaresidins. Perhaps the most abundant azetidine containing natural product is azetidine-2-carboxylic acid, a toxic homolog of proline.