We would like to thank the School of Physical Sciences of the University of California, Irvine, for generous startup funding. Acknowledgement is made to the donors of the American Chemical Society Petroleum Research Fund for partial support of this research through a Type G Starter Grant. New faculty awards from Amgen and Eli Lilly are also gratefully acknowledged. We also thank Joel Silverston for experimental assistance.
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Communication
Synthesis of Nitrogen Heterocycles by the Ring Opening of Pyridinium Salts†
Article first published online: 30 OCT 2006
DOI: 10.1002/anie.200602996
Copyright © 2006 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Issue
Angewandte Chemie International Edition
Volume 45, Issue 46, pages 7803–7806, November 27, 2006
Additional Information
How to Cite
Kearney, A. M. and Vanderwal, C. D. (2006), Synthesis of Nitrogen Heterocycles by the Ring Opening of Pyridinium Salts. Angew. Chem. Int. Ed., 45: 7803–7806. doi: 10.1002/anie.200602996
- †
Publication History
- Issue published online: 20 NOV 2006
- Article first published online: 30 OCT 2006
- Manuscript Received: 25 JUL 2006
Funded by
- American Chemical Society Petroleum Research Fund
Keywords:
- biaryls;
- cyclization;
- indoles;
- nitrogen heterocycles;
- pyridinium salts
The century-old ring-opening reaction of pyridinium salts with tethered nucleophiles has been harnessed for a synthesis of substituted indoles and related nitrogen heterocyles. Extension of this method could lead to oxygen- and sulfur-containing heterocycles and carbocycles, as well as to applications in natural product synthesis and medicinal chemistry.