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Vinyl-1,2,4-oxadiazoles Behave as Nucleophilic Partners in Morita–Baylis–Hillman Reactions

Author:
Fernandes, Fábio S., Rodrigues, Manoel T., Zeoly, Lucas A., Conti, Caroline, Angolini, Célio F. F., Eberlin, Marcos Nogueira, Coelho, Fernando
Source:
Journal of organic chemistry 2018 v.83 no.24 pp. 15118-15127
ISSN:
1520-6904
Subject:
Lewis bases, aldehydes, amino alcohols, bioactive properties, chemical reactions, chemical structure, heterocyclic compounds, organic chemistry, solvents
Abstract:
We describe that vinyl-oxadiazoles function as a new and efficient nucleophilic partner for the Morita–Baylis–Hillman (MBH) reaction. The reaction between 5-vinyl-3-aryl-1,2,4-oxadiazoles and aromatic and aliphatic aldehydes, catalyzed by DABCO in the absence of solvent, showed high efficiency to afford a new class of heterocyclic MBH adducts with potential biological activity on yields up to 99% and short reaction times. These synthetically attractive adducts bear a heterocyclic scaffold of large pharmaceutical and commercial interest associated with a plethora of biological effects and technological applications. We also demonstrate their synthetic usefulness by a photoinduced addition reaction to a polyfunctionalized amino alcohol.
Agid:
6266400