Misplaced Pages

1,3,4-Oxadiazole

Article snapshot taken from Wikipedia with creative commons attribution-sharealike license. Give it a read and then ask your questions in the chat. We can research this topic together.
1,3,4-Oxadiazole
Names
Preferred IUPAC name 1,3,4-Oxadiazole
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C2H2N2O/c1-3-4-2-5-1/h1-2HKey: FKASFBLJDCHBNZ-UHFFFAOYSA-N
SMILES
  • C1=NN=CO1
Properties
Chemical formula C2H2N2O
Molar mass 70.051 g·mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

1,3,4-Oxadiazole is a nitrogen and oxygen containing heterocycle, and one of the four isomers of oxadiazole.

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. One pathway is from oxidation of tetrazoles in the presence of aldehydes. Similarly, the reaction of tetrazoles with acyl chlorides provides oxadiazoles. Both methods involve the release of N2.

See also

References

  1. PubChem. "1,3,4-Oxadiazole". pubchem.ncbi.nlm.nih.gov. National Center for Biotechnology Information, U.S. National Library of Medicine. Retrieved 2019-07-22.
  2. 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. PMC 4131560. PMID 25147788.
  3. "1,3,4-Oxadiazole synthesis". www.organic-chemistry.org. Retrieved 11 November 2018.
  4. 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.
  5. Wong, Michael Y.; Krotkus, Simonas; Copley, Graeme; Li, Wenbo; Murawski, Caroline; Hall, David; Hedley, Gordon J.; Jaricot, Marie; Cordes, David B.; Slawin, Alexandra M. Z.; Olivier, Yoann; Beljonne, David; Muccioli, Luca; Moral, Monica; Sancho-Garcia, Juan-Carlos; Gather, Malte C.; Samuel, Ifor D. W.; Zysman-Colman, Eli (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. hdl:10023/18433. PMID 30192504.
Category: