Summary
Isoxazole is an azole with an oxygen atom next to the nitrogen. It is also the class of compounds containing this ring. Isoxazolyl is the univalent radical derived from isoxazole.
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| Preferred IUPAC name
1,2-Oxazole[1] | |||
| Other names
isoxazole
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3D model (JSmol)
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| ECHA InfoCard | 100.005.472 | ||
PubChem CID
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CompTox Dashboard (EPA)
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| Properties | |||
| C3H3NO | |||
| Molar mass | 69.06202 g/mol | ||
| Density | 1.075 g/ml | ||
| Boiling point | 95 °C (203 °F; 368 K) | ||
| Acidity (pKa) | -3.0 (of conjugate acid)[2] | ||
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references
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OccurrenceEdit
Isoxazole rings are found in some natural products, such as ibotenic acid and muscimol.
SynthesisEdit
Isoxazole can be synthesised via a variety of methods.[3][4] Examples include via a 1,3-dipolar cycloaddition of nitrile oxides with alkynes; or the reaction of hydroxylamine with 1,3-diketones or derivatives of propiolic acid.[5]
Pharmaceuticals and herbicidesEdit
Isoxazoles also form the basis for a number of drugs,[6] including the COX-2 inhibitor valdecoxib (Bextra) and a neurotransmitter agonist AMPA. A derivative, furoxan, is a nitric oxide donor. An isoxazolyl group is found in many beta-lactamase-resistant antibiotics, such as cloxacillin, dicloxacillin and flucloxacillin. Leflunomide is an isoxazole-derivative drug. Examples of AAS containing the isoxazole ring include danazol and androisoxazole. A number of pesticides are isoxazoles.[7]
See alsoEdit
ReferencesEdit
- ^ International Union of Pure and Applied Chemistry (2014). Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013. The Royal Society of Chemistry. p. 140. doi:10.1039/9781849733069. ISBN 978-0-85404-182-4.
- ^ Zoltewicz, J. A. & Deady, L. W. Quaternization of heteroaromatic compounds. Quantitative aspects. Adv. Heterocycl. Chem. 22, 71-121 (1978)
- ^ Dasa S, Chanda K (2021). "An overview of metal-free synthetic routes to isoxazoles: the privileged scaffold". RSC Adv (11): 32680–32705. doi:10.1039/D1RA04624A.
- ^ Morita, Taiki; Yugandar, Somaraju; Fuse, Shinichiro; Nakamura, Hiroyuki (March 2018). "Recent progresses in the synthesis of functionalized isoxazoles". Tetrahedron Letters. 59 (13): 1159–1171. doi:10.1016/j.tetlet.2018.02.020.
- ^ Hossain M, Khan M, Kim S, Le H (2022). "Synthesis of 3,4,5-trisubstituted isoxazoles in water via a [3 + 2]-cycloaddition of nitrile oxides and 1,3-diketones, β-ketoesters, or β-ketoamides". Beilstein J. Org. Chem. (18): 446–458. doi:10.3762/bjoc.18.47. PMID 35529890.
- ^ Zhu, Jie; Mo, Jun; Lin, Hong-zhi; Chen, Yao; Sun, Hao-peng (2018). "The recent progress of isoxazole in medicinal chemistry". Bioorganic & Medicinal Chemistry. 26 (12): 3065–3075. doi:10.1016/j.bmc.2018.05.013.
{{cite journal}}: CS1 maint: uses authors parameter (link) - ^ Clemens Lamberth (2018). "Oxazole and Isoxazole Chemistry in Crop Protection". Journal of Heterocyclic Chemistry. 55 (9): 2035–2045. doi:10.1002/jhet.3252.
External linksEdit
- Synthesis of isoxazoles (overview of recent methods)