» Articles » PMID: 32952727

Access to Highly Substituted Oxazoles by the Reaction of α-azidochalcone with Potassium Thiocyanate

Overview
Specialty Chemistry
Date 2020 Sep 21
PMID 32952727
Authors
Affiliations
Soon will be listed here.
Abstract

The reactivity of α-azidochalcones has been explored for the preparation of highly substituted oxazoles via a 2-azirine intermediate. The azidochalcones, when treated with potassium thiocyanate in the presence of potassium persulfate, lead to 2,4,5-trisubstituted oxazoles in good yields. Incidentally, 2-aminothiazoles are the products when ferric nitrate is employed instead of persulfate in the above reaction.

References
1.
Yang W, Shimada K, Delva D, Patel M, Ode E, Skouta R . Identification of Simple Compounds with Microtubule-Binding Activity That Inhibit Cancer Cell Growth with High Potency. ACS Med Chem Lett. 2012; 3(1):35-38. PMC: 3256933. DOI: 10.1021/ml200195s. View

2.
Annadurai S, Martinez R, Canney D, Eidem T, Dunman P, Abou-Gharbia M . Design and synthesis of 2-aminothiazole based antimicrobials targeting MRSA. Bioorg Med Chem Lett. 2012; 22(24):7719-25. DOI: 10.1016/j.bmcl.2012.09.095. View

3.
Yamada K, Kamimura N, Kunishima M . Development of a method for the synthesis of 2,4,5-trisubstituted oxazoles composed of carboxylic acid, amino acid, and boronic acid. Beilstein J Org Chem. 2017; 13:1478-1485. PMC: 5550800. DOI: 10.3762/bjoc.13.146. View

4.
Perner R, Koenig J, DiDomenico S, Gomtsyan A, Schmidt R, Lee C . Synthesis and biological evaluation of 5-substituted and 4,5-disubstituted-2-arylamino oxazole TRPV1 antagonists. Bioorg Med Chem. 2010; 18(13):4821-9. DOI: 10.1016/j.bmc.2010.04.099. View

5.
Liu R, Huang Z, Murray M, Guo X, Liu G . Quinoxalin-2(1H)-one derivatives as inhibitors against hepatitis C virus. J Med Chem. 2011; 54(16):5747-68. DOI: 10.1021/jm200394x. View