Azetidine is a saturated

heterocyclic A heterocyclic compound or ring structure is a cyclic compound that has atoms of at least two different elements as members of its ring(s). Heterocyclic organic chemistry is the branch of organic chemistry dealing with the synthesis, proper ...

organic compound Some chemical authorities define an organic compound as a chemical compound that contains a carbon–hydrogen or carbon–carbon bond; others consider an organic compound to be any chemical compound that contains carbon. For example, carbon-co ...

containing three

carbon Carbon () is a chemical element; it has chemical symbol, symbol C and atomic number 6. It is nonmetallic and tetravalence, tetravalent—meaning that its atoms are able to form up to four covalent bonds due to its valence shell exhibiting 4 ...

atoms and one

nitrogen Nitrogen is a chemical element; it has Symbol (chemistry), symbol N and atomic number 7. Nitrogen is a Nonmetal (chemistry), nonmetal and the lightest member of pnictogen, group 15 of the periodic table, often called the Pnictogen, pnictogens. ...

atom. It is a liquid at room temperature with a strong odor of ammonia and is strongly

basic Basic or BASIC may refer to: Science and technology * BASIC, a computer programming language * Basic (chemistry), having the properties of a base * Basic access authentication, in HTTP Entertainment * Basic (film), ''Basic'' (film), a 2003 film ...

compared to most secondary amines.

Synthesis and occurrence

Azetidines can be prepared by reduction of azetidinones (β-lactams) with

lithium aluminium hydride Lithium aluminium hydride, commonly abbreviated to LAH, is an inorganic compound with the chemical formula or . It is a white solid, discovered by Finholt, Bond and Schlesinger in 1947. This compound is used as a reducing agent in organic synthe ...

. Even more effective is a mixture of lithium aluminium hydride and

aluminium trichloride Aluminium chloride, also known as aluminium trichloride, is an inorganic compound with the formula . It forms a hexahydrate with the formula , containing six water molecules of hydration. Both the anhydrous form and the hexahydrate are col ...

, a source of "AlClH₂" and "AlCl₂H". Azetidine can also be produced by a multistep route from

3-amino-1-propanol 3-Amino-1-propanol is the organic compound Some chemical authorities define an organic compound as a chemical compound that contains a carbon–hydrogen or carbon–carbon bond; others consider an organic compound to be any chemical compound ...

. Regio- and diastereoselective synthesis of 2-arylazetidines could be performed from appropriately substituted oxiranes via ring transformation. It is controlled by Baldwin's Rules with remarkable functional group tolerance. The Paternò−Büchi reaction has an ''aza'' analogue. 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 Azetidine-2-carboxylic acid (abbreviated Aze or Azc) is a plant Non-proteinogenic amino acids, non-protein amino acid homologue of proline with the molecular formula C4H7NO2. Aze is a heterocyclic, 4 membered ring with nitrogen as its heteroatom ( ...

- a toxic mimic of

proline Proline (symbol Pro or P) is an organic acid classed as a proteinogenic amino acid (used in the biosynthesis of proteins), although it does not contain the amino group but is rather a secondary amine. The secondary amine nitrogen is in the p ...

References

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External links

ChemSynthesis

Synthesis and occurrence

See also

References

External links