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.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.