Mackenzie Presbiterian University , São Paulo , São Paulo 01302-907 , Brazil.
J Org Chem. 2018 Dec 21;83(24):15118-15127. doi: 10.1021/acs.joc.8b02402. Epub 2018 Dec 4.
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.
我们描述了乙烯基-噁二唑可以作为一种新的、有效的亲核试剂，用于 Morita-Baylis-Hillman（MBH）反应。在无溶剂存在下，DABCO 催化 5-乙烯基-3-芳基-1,2,4-噁二唑与芳香族和脂肪族醛之间的反应，以高产率（高达 99%）和短反应时间得到了一类新的具有潜在生物活性的杂环 MBH 加合物。这些具有吸引力的合成加合物具有大的医药和商业利益的杂环支架，与众多的生物效应和技术应用相关。我们还通过多官能化氨基醇的光诱导加成反应证明了它们的合成用途。
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