Synthesis of a Biologically Active Oxazol-5-(4H)-one via an Erlenmeyer–Plöchl Reaction

Synthesis of a Biologically Active Oxazol-5-(4H)-one via an Erlenmeyer–Plöchl Reaction

The synthesis of (Z)-4-(4-nitrobenzylidene)-2-phenyloxazol-5(4H)-one, which is a potent immunomodulator and tyrosinase inhibitor, is described as an experiment for an upper-division undergraduate organic chemistry laboratory course. This compound is produced via an Erlenmeyer-Plochl reaction in the...

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Bibliographic Details
Published in:Journal of chemical education Vol. 92; no. 9; pp. 1543 - 1546
Main Authors: Rodrigues, Catarina A. B., Martinho, José M. G., Afonso, Carlos A. M.
Format: Journal Article
Language:English
Published: Easton American Chemical Society 08-09-2015
Subjects:
Chemical reactions
Chemical synthesis
Chromatography
Immunomodulators
Organic chemistry
Solvents
Tyrosinase
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Summary:The synthesis of (Z)-4-(4-nitrobenzylidene)-2-phenyloxazol-5(4H)-one, which is a potent immunomodulator and tyrosinase inhibitor, is described as an experiment for an upper-division undergraduate organic chemistry laboratory course. This compound is produced via an Erlenmeyer-Plochl reaction in the absence of any additional solvents and is isolated without need of preparative chromatography, yielding up to 97% of product.
ISSN:0021-9584
1938-1328
DOI:10.1021/ed500212t