Chemistry: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 (β-lactams) with lithium aluminium hydride. Even more effective is a mixture of lithium aluminium hydride and aluminium trichloride, a source of "AlClH2" and "AlCl2H".[1]
Azetidine can also be produced by a multistep route from 1,3-disubstituted alkanes. Thus, for example, a multistep route builds azetidine from 3-amino-1-propanol, acrylic acid, thionyl chloride, and base;[2] likewise, azetidine dicarboxylic acids form when glutaric anhydride is brominated (at the α position) and then aminated.[3]
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.[4]
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 - a toxic mimic of proline.[citation needed]
See also
- Azete, the unsaturated analog
References
- ↑ Alcaide, Benito; Almendros, Pedro; Aragoncillo, Cristina (2007). "Β-Lactams: Versatile Building Blocks for the Stereoselective Synthesis of Non-β-Lactam Products". Chemical Reviews 107 (11): 4437–4492. doi:10.1021/cr0307300. PMID 17649981.
- ↑ Donald H. Wadsworth (1973). "Azetidine". Organic Syntheses 53: 13. doi:10.15227/orgsyn.053.0013.
- ↑ Kozikowski, Alan P.; Tückmantel, Werner; Reynolds, Ian J.; Wroblewski, Jarda T. (1990). "Synthesis and bioactivity of a new class of rigid glutamate analogues". Journal of Medicinal Chemistry (American Chemical Society) 33 (6). doi:10.1021/jm00168a007.
- ↑ Kovács, Ervin; Ferenc, Faigl; Zoltan, Mucsi (Aug 10, 2020). "Regio- and Diastereoselective Synthesis of 2-Arylazetidines. Quantum Chemical Explanation of Baldwin's Rules for the Ring-formation Reactions of Oxiranes.". Journal of Organic Chemistry 85 (17): 11226–11239. doi:10.1021/acs.joc.0c01310. PMID 32786621.
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