The synthesis of 5-[2-(trifluoromethylheteroaryl)-ethyl]-1,3,4-oxadiazoles derived from levulinic acid is reported. Cyclocondensations [4 + 1] between four different 5-[2-(trifluoromethylheteroaryl) propionylhydrazides derived from methyl 7,7,7-trifluoro-4-methoxy-6-oxo-4-heptenoate obtained from levulinic acid, and electrophilic orthoesters RC(OR1)3 (where R = H, Me, Ph) and CS2 were carried out in a mild medium. Good yields (69-96%) of isolated products were obtained. The structures of the new ethylene-spaced biheterocycles were characterized using1H and 13C nuclear magnetic resonance (NMR) spectroscopy and electrospray ionization coupled to tandem mass spectrometric (ESI MS/MS) data.
CITATION STYLE
Malavolta, J. L., Frigo, L. M., Moura, S., Flores, D. C., & Flores, A. F. C. (2017). Strategies for the efficient synthesis of biheterocyclic 5-[2-(trifluoromethylheteroaryl)-ethyl]-1,3,4-oxadiazoles from levulinic acid. Journal of the Brazilian Chemical Society, 28(11), 2106–2116. https://doi.org/10.21577/0103-5053.20170056
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