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Synthesis of alkaloid-like compounds via the bridging Ritter reactions II

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Abstract

The bridging Ritter reactions are considered to be efficient synthetic methods rapidly providing access to alkaloid-like compounds in a few steps from inexpensive starting materials. In this manuscript, we report the synthesis of benzo[c]azepine derivatives bearing either amide or hydroxyl groups via the bridging Ritter reactions. These compounds are diastereoisomers of a known AChE inhibitor. All the structures were fully characterised by NMR spectroscopy and high-resolution mass spectrometry. NMR spectral analysis of diastereoisomers has allowed for the relative stereochemistry of the AChE inhibitor to be established.

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Acknowledgments

We thank Dr. Ronald Shimmon for the NMR training and technical support and Faculty of Science UTS for supporting this project.

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Authors and Affiliations

  1. School of Mathematical and Physical Sciences, University of Technology Sydney, PO Box 123, Broadway, NSW, 2007, Australia

    Alison T. Ung, Alexander N. West, Matthew J. A. Phillips & Steven G. Williams

Authors
  1. Alison T. Ung
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  2. Alexander N. West
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  3. Matthew J. A. Phillips
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  4. Steven G. Williams
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Correspondence to Alison T. Ung.

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Ung, A.T., West, A.N., Phillips, M.J.A. et al. Synthesis of alkaloid-like compounds via the bridging Ritter reactions II. Monatsh Chem 147, 1737–1746 (2016). https://doi.org/10.1007/s00706-016-1817-4

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  • DOI: https://doi.org/10.1007/s00706-016-1817-4

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