Department of Chemistry, Tarbiat Modares University, PO Box 14115-175, Tehran, Iran.
Org Biomol Chem. 2022 Jun 1;20(21):4352-4360. doi: 10.1039/d2ob00277a.
A new strategy for the construction of functionalized 2-amino-3-cyano pyrroles has been developed. The reactions involved a copper-catalyzed azide-alkyne cycloaddtion reaction between terminal alkynes and sulfonyl azides followed by generation of -sulfonoketenimine intermediates. Interception of these reactive ketenimines by phenacylmalononitriles in the presence of copper(I) iodide and EtN afforded the expected products. The reaction proceeded smoothly in THF at ambient temperature to afford the target compounds in 70-92% yields and excellent regioselectivity. Evidence for the structure of a typical product is obtained from single-crystal X-ray analyses.
一种构建功能化 2-氨基-3-氰基吡咯的新策略已经开发出来。该反应涉及末端炔烃和磺酰叠氮之间的铜催化叠氮-炔环加成反应，然后生成 -磺酰基亚胺中间体。在碘化亚铜和三乙胺的存在下，这些反应性的亚胺中间体被苯甲酰基丙二腈捕获，得到预期的产物。反应在四氢呋喃中于室温下顺利进行，以 70-92%的产率和优异的区域选择性得到目标化合物。典型产物的结构证据来自单晶 X 射线分析。
