Cannalire Rolando, Russo Camilla, Luciano Paolo, Cerra Bruno, Gioiello Antimo, Brunelli Francesca, Tron Gian Cesare, Giustiniano Mariateresa
Department of Pharmacy, University of Naples Federico II, via D. Montesano 49, 80131, Napoli, Italy.
Laboratory of Medicinal and Advanced Synthetic Chemistry (Lab MASC), Department of Pharmaceutical Sciences, University of Perugia, Via del Liceo 1, 06123, Perugia, Italy.
Mol Divers. 2023 Feb;27(1):511-515. doi: 10.1007/s11030-022-10418-4. Epub 2022 Apr 13.
A new Lewis acid promoted domino isocyanide insertion/5-exo-dig cyclization of readily available Strecker 3-component adducts to 4-substituted 5-aminoimidazole derivatives is herein reported. Despite their potential as relevant heterocyclic scaffolds in medicinal chemistry programs, this class of compounds is still underrepresented, with current synthetic strategies poorly efficient in terms of timing and yields. To this end, we show how the exploitation of unconventional reactivities of isocyanides, promoted by ytterbium-triflate, could represent a key resource to enable a fast and easy access to such an unexplored area of the chemical space.
本文报道了一种新型路易斯酸促进的多米诺异腈插入/5-外向-环化反应，该反应可将易得的施特雷克三组分加合物转化为4-取代的5-氨基咪唑衍生物。尽管这类化合物在药物化学项目中作为相关杂环骨架具有潜在价值，但目前这类化合物的研究仍较少，现有的合成策略在反应时间和产率方面效率较低。为此，我们展示了如何利用三氟甲磺酸镱促进的异腈的非常规反应性，这可能是快速简便地进入这一未开发化学空间领域的关键资源。
