Chemistry:1,3,4-Oxadiazole
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| Preferred IUPAC name
1,3,4-Oxadiazole | |
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3D model (JSmol)
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| Properties | |
| C2H2N2O | |
| Molar mass | 70.051 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
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Tracking categories (test):
1,3,4-Oxadiazole is a nitrogen and oxygen containing heterocycle, and one of the four isomers of oxadiazole.[1][2]
Derivatives
1,3,4-Oxadiazole itself is not commonly used in organic chemistry, but many of its derivatives are important. For example, raltegravir is an HIV drug which contains an 1,3,4-oxadiazole ring. Other pharmaceutical drugs containing the 1,3,4-oxadiazole ring include fenadiazole, zibotentan, and tiodazosin.
1,3,4-Oxadiazole derivatives can be synthesized in a variety of ways.[3] One pathway is from oxidation of tetrazoles in the presence of aldehydes.[4] Similarly, the reaction of tetrazoles with acyl chlorides provides oxadiazoles.[5] Both methods involve the release of N2.
See also
- Furazan (1,2,5-oxadiazole)
References
- ↑ PubChem. "1,3,4-Oxadiazole" (in en). National Center for Biotechnology Information, U.S. National Library of Medicine. https://pubchem.ncbi.nlm.nih.gov/compound/97428.
- ↑ Bala, Suman; Kamboj, Sunil; Kajal, Anu; Saini, Vipin; Prasad, Deo Nanadan (2014). "1,3,4-Oxadiazole Derivatives: Synthesis, Characterization, Antimicrobial Potential, and Computational Studies". BioMed Research International 2014: 172791. doi:10.1155/2014/172791. PMID 25147788.
- ↑ "1,3,4-Oxadiazole synthesis". https://www.organic-chemistry.org/synthesis/heterocycles/1,3,4-oxadiazoles.shtm. Retrieved 11 November 2018.
- ↑ Wang, Liang; Cao, Jing; Chen, Qun; He, Mingyang (17 April 2015). "One-Pot Synthesis of 2,5-Diaryl 1,3,4-Oxadiazoles via Di-tert-butyl Peroxide Promoted Acylation of Aryl Tetrazoles with Aldehydes". The Journal of Organic Chemistry 80 (9): 4743–4748. doi:10.1021/acs.joc.5b00207. PMID 25860162.
- ↑ Wong, Michael Y.; Krotkus, Simonas; Copley, Graeme; Li, Wenbo; Murawski, Caroline; Hall, David; Hedley, Gordon J.; Jaricot, Marie et al. (7 September 2018). "Deep-Blue Oxadiazole-Containing Thermally Activated Delayed Fluorescence Emitters for Organic Light-Emitting Diodes". ACS Applied Materials & Interfaces 10 (39): 33360–33372. doi:10.1021/acsami.8b11136. PMID 30192504.
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