European Journal of Organic Chemistry 2018-03-15

A Highly Chemoselective Synthesis of Cyclic Divalent Propargylamines by Copper‐Catalyzed Annulation/Double A3‐Couplings

huangdi feng; Yazhen Zhang; Xiaohui Liu; Liliang Huang

Index: 10.1002/ejoc.201800393

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Abstract

Divalent propargylamines are a pre‐eminent class of intermediates to multidentate ligands which have wide implications for use in catalysis. Here, a highly chemoselective and versatile protocol for the construction of novel cyclic divalent propargylamines has been accomplished under microwave irradiation. This sequential transformation comprises a copper‐catalyzed annulation/ A3‐coupling/A3‐coupling of a primary diamine with formaldehyde solution, and two alkynes, directly providing a diverse set of N,N'‐dipropargyl imidazolidines and hexahydropyrimidines in the moderate to excellent yields.