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Publication Details:

Title: Gold-catalyzed cyclization and cycloisomerization of yne-tethered ynamide: the significance of a masked enol-equivalent of an amide

Author(s)Sanatan Nayak, B Prabagar, Akhila K Sahoo : Organic & biomolecular chemistry, 2016, 14 (3), 803-807 (Invited Prospective).
Journal NameOrganic & biomolecular chemistry
journal image URLhttp://chemistry.uohyd.ac.in/~aks/wp-content/uploads/sanatanobccover.png

More Details:


This perspective briefly describes the conceptual manifestation of a Brønsted acid promoted Au-catalyzed cyclization of yne-tethered ynamides for the construction of novel N-heterocycles. A hetero-atom assisted intramolecular 6-endo-dig cyclization of a transient ketene N,O-acetal (a masked enol-ether of an amide), generated from an ambivalent ynamide through the attack of p-TsOH, with a Au-activated yne-motif creates dihydropyridinones and benzo[f]dihydroisoquinolones. The Au(I)-catalyzed cycloisomerization of an alkyne-tethered ketene N,N-acetal to manufacture unusual cyclobutene-fused azepine scaffolds is also highlighted.

https://pubs.rsc.org/en/content/articlelanding/2016/ob/c5ob02262b#!divAbstract