We acknowledge the Donors of the American Chemical Society Petroleum Research Fund for partial support of this research. We are also grateful for financial support from the University of Utah Research Foundation.
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Communication
Addition–Hydroamination Reactions of Propargyl Cyanamides: Rapid Access to Highly Substituted 2-Aminoimidazoles†
Article first published online: 25 MAR 2009
DOI: 10.1002/anie.200900160
Copyright © 2009 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Additional Information
How to Cite
Giles, R., Sullivan, J., Steiner, A. and Looper, R. (2009), Addition–Hydroamination Reactions of Propargyl Cyanamides: Rapid Access to Highly Substituted 2-Aminoimidazoles. Angewandte Chemie International Edition, 48: 3116–3120. doi: 10.1002/anie.200900160
- †
Publication History
- Issue published online: 7 APR 2009
- Article first published online: 25 MAR 2009
- Manuscript Received: 10 JAN 2009
Funded by
- American Chemical Society Petroleum Research Fund
- University of Utah Research Foundation
Keywords:
- 2-aminoimidazoles;
- cyanamides;
- heterocycles;
- hydroamination;
- natural products
Graphical Abstract
A valuable pharmacophore, the 2-aminoimidazole moiety, can be accessed with a variety of substitution patterns through an addition–hydroamination–isomerization sequence (see scheme; R1,R4,R5=alkyl; R3=alkyl, aryl; R2=H, alkyl, aryl). The synthesis of the propargyl cyanamide precursors through a three-component coupling enables the preparation of this important heterocyclic core structure in just three steps.
Abstract
A valuable pharmacophore, the 2-aminoimidazole moiety, can be accessed with a variety of substitution patterns through an addition–hydroamination–isomerization sequence (see scheme; R1,R4,R5=alkyl; R3=alkyl, aryl; R2=H, alkyl, aryl). The synthesis of the propargyl cyanamide precursors through a three-component coupling enables the preparation of this important heterocyclic core structure in just three steps.