Tehran University of Medical Sciences

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Potassium Carbonate Catalyzed Intramolecular Post-Ugi Hydroamination Reaction Leading to N -Aryl Piperazine Derivatives Publisher



Yazzaf R1 ; Sayahi MH2 ; Mahdavi M3
Authors
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Authors Affiliations
  1. 1. School of Chemistry, College of Science, University of Tehran, PO Box 14155-6455, Tehran, Iran
  2. 2. Department of Chemistry, Payame Noor University, Tehran, Iran
  3. 3. Endocrinology and Metabolism Research Center, Endocrinology and Metabolism Clinical Sciences Institute, Tehran University of Medical Sciences, Tehran, Iran

Source: Synlett Published:2025


Abstract

N -Arylpiperazines are prominent structures found in natural products and synthetic chemical entities, including therapeutic agents. In this work, we introduce a novel strategy for the effective synthesis of distinctive piperazine compounds through a post-Ugi cyclization under transition-metal-free conditions. This method involves the formation of a four-component Ugi adduct by combining an aldehyde, an isocyanide, a primary propargylamine, and an oxamic acid. Subsequently, an intramolecular alkyne hydroamination reaction occurs, leading to the formation of a piperazine derivative through carbon-nitrogen bond formation. The products have been characterized by 1 H and 13 C NMR spectroscopy. © 2025 Georg Thieme Verlag. All rights reserved.