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Aza-Morita–Baylis–Hillman Reaction with Vinyl-oxadiazoles: An Expeditious Approach to Access New Heterocyclic Arrangements
Synlett ( IF 2 ) Pub Date : 2019-11-25 , DOI: 10.1055/s-0039-1691497
André Capretz-Agy , Fábio S. Fernandes , Manoel T. Rodrigues , Caroline Conti , Fernando Coelho

In this communication, we disclosed a new aza-MBH reaction in which traditional nucleophilic partners of these reactions (e.g., acrylates, nitroolefins or enones) were replaced by vinyl-1,2,4-oxadiazoles. Thus, the aza-MBH reaction between 5-aryl-3-vinyl-1,2,4-oxadiazoles and N-sulfonylimines, catalyzed by the mixture DABCO/AcOH, provides a class of new adduct in yields varying from 31% up to 93% in reaction times from 30 minutes to 24 hours. Due to the biological activities and technological applications associated with the 1,2,4-oxadiazole motifs, this new class of heterocycles offers great synthetic and commercial potentiality.

中文翻译:

Aza-Morita-Baylis-Hillman 反应与乙烯基恶二唑:获得新杂环排列的快速方法

在这篇通讯中,我们公开了一种新的氮杂-MBH 反应,其中这些反应的传统亲核伙伴(例如,丙烯酸酯、硝基烯烃或烯酮)被乙烯基-1,2,4-恶二唑取代。因此,由 DABCO/AcOH 混合物催化的 5-芳基-3-乙烯基-1,2,4-恶二唑和 N-磺酰亚胺之间的氮杂-MBH 反应提供了一类新的加合物,产率从 31% 到93% 的反应时间从 30 分钟到 24 小时。由于与 1,2,4-恶二唑基序相关的生物活性和技术应用,这类新型杂环具有巨大的合成和商业潜力。
更新日期:2019-11-25
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