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Diversity-Oriented Synthesis of Hydrazine-Derived Compounds from Amino Isocyanates Generated In Situ†

Authors

  • Christian Clavette,

    1. Centre for Catalysis Research and Innovation, Department of Chemistry, University of Ottawa, 10 Marie-Curie, Ottawa, ON K1N 6N5 (Canada)
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    • These authors contributed equally to this work.

  • Jean-François Vincent Rocan,

    1. Centre for Catalysis Research and Innovation, Department of Chemistry, University of Ottawa, 10 Marie-Curie, Ottawa, ON K1N 6N5 (Canada)
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    • These authors contributed equally to this work.

  • Prof. Dr. André M. Beauchemin

    Corresponding author
    1. Centre for Catalysis Research and Innovation, Department of Chemistry, University of Ottawa, 10 Marie-Curie, Ottawa, ON K1N 6N5 (Canada)

    • Centre for Catalysis Research and Innovation, Department of Chemistry, University of Ottawa, 10 Marie-Curie, Ottawa, ON K1N 6N5 (Canada)

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  • †

    We thank the University of Ottawa, NSERC (DAS, CREATE, and CRD grants to A.M.B.), CFI, and the Ontario MRI for generous financial support. Support of related work by AstraZeneca Canada and OmegaChem is gratefully acknowledged. C.C. and J.-F.V.R. thank NSERC (CREATE on medicinal chemistry and biopharmaceutical development) and OGS (C.C.) for scholarships.

Abstract

original image

Behind the mask: Nitrogen-substituted isocyanates are rare and their synthetic potential is virtually untapped. Simple masked precursors can form amphoteric amino isocyanate intermediates in situ, and allows the synthesis of complex hydrazine derivatives upon addition with amines. This reactivity was used in a cascade substitution/hydroamination sequence, and in the assembly of azadipeptide analogues.

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Article Information

DOI

10.1002/anie.201306379

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Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim

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Keywords

  • azapeptides;
  • hydroamination;
  • microwave chemistry;
  • nitrogen heterocycles;
  • synthetic methods

Publication History

  • Issue online:
  • Version of record online:
  • Manuscript Received:

Funded by

  • University of Ottawa
  • NSERC
  • CFI
  • Ontario MRI

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Citing Literature

  • Number of times cited: 14
  1. 1Jean-François Vincent-Rocan, Ryan A. Ivanovich, Christian Clavette, Kyle Leckett, Julien Bejjani, André M. Beauchemin, Cascade reactions of nitrogen-substituted isocyanates: a new tool in heterocyclic chemistry, Chem. Sci., 2016, 7, 1, 315CrossRef
  2. 2Jing An, Howard Alper, André M. Beauchemin, Copper-Catalyzed Cascade Substitution/Cyclization ofN-Isocyanates: A Synthesis of 1-Aminobenzimidazolones, Organic Letters, 2016, 18, 14, 3482CrossRef
  3. 3Joshua S. Derasp, Jean-François Vincent-Rocan, André M. Beauchemin, Divergent Reactivity ofN-Isocyanates with Primary and Secondary Amines: Access to Pyridazinones and Triazinones, Organic Letters, 2016, 18, 4, 658CrossRef
  4. 4Xingao Peng, Atsushi Kaga, Hajime Hirao, Shunsuke Chiba, Hydroamination of alkenyl N-arylhydrazones mediated by t-BuOK for the synthesis of nitrogen heterocycles, Org. Chem. Front., 2016, 3, 5, 609CrossRef
  5. 5Ryan A. Ivanovich, Christian Clavette, Jean-François Vincent-Rocan, Jean-Grégoire Roveda, Serge I. Gorelsky, André M. Beauchemin, Intramolecular Alkene Aminocarbonylation Using Concerted Cycloadditions of Amino-Isocyanates, Chemistry - A European Journal, 2016, 22, 23, 7906Wiley Online Library
  6. 6Akinari Sumita, Yuko Otani, Tomohiko Ohwada, Tandem buildup of complexity of aromatic molecules through multiple successive electrophile generation in one pot, controlled by varying the reaction temperature, Org. Biomol. Chem., 2016, 14, 5, 1680CrossRef
  7. 7Jean-François Vincent-Rocan, Christian Clavette, Kyle Leckett, André M. Beauchemin, A Cascade Synthesis of Aminohydantoins Using In Situ-GeneratedN-Substituted Isocyanates, Chemistry - A European Journal, 2015, 21, 10, 3886Wiley Online Library
  8. 8Jeffrey D. St. Denis, Zhi He, Andrei K. Yudin, Amphoteric α-Boryl Aldehyde Linchpins in the Synthesis of Heterocycles, ACS Catalysis, 2015, 5, 9, 5373CrossRef
  9. 9Jean-François Vincent-Rocan, Joshua S. Derasp, André M. Beauchemin, Diversity-oriented heterocyclic synthesis using divergent reactivity of N-substituted iso(thio)cyanates, Chem. Commun., 2015, 51, 91, 16405CrossRef
  10. 10Ryan A. Ivanovich, Jean-François Vincent-Rocan, Eslam B. Elkaeed, André M. Beauchemin, One-Pot Synthesis of Aza-Diketopiperazines Enabled by Controlled Reactivity ofN-Isocyanate Precursors, Organic Letters, 2015, 17, 19, 4898CrossRef
  11. 11Tayseer Mahdi, Douglas W. Stephan, Stoichiometric and Catalytic Inter- and Intramolecular Hydroamination of Terminal Alkynes by Frustrated Lewis Pairs, Chemistry - A European Journal, 2015, 21, 31, 11134Wiley Online Library
  12. 12Jiaan Shao, Xingyu Liu, Ke Shu, Pai Tang, Jing Luo, Wenteng Chen, Yongping Yu, Tuning the Annulation Reactivity of Vinyl Azides and Carbazates: A Divergent Synthesis of Aza-pyrimidinones and Imidazoles, Organic Letters, 2015, 17, 18, 4502CrossRef
  13. 13Christian Clavette, Jean-Francois Vincent Rocan, Andre M. Beauchemin, ChemInform Abstract: Diversity-Oriented Synthesis of Hydrazine-Derived Compounds from Amino Isocyanates Generated in situ., ChemInform, 2014, 45, 18, noWiley Online Library
  14. 14Isabelle Dion, Jean-François Vincent-Rocan, Lei Zhang, Pamela H. Cebrowski, Marie-Eve Lebrun, Jennifer Y. Pfeiffer, Anne-Catherine Bédard, André M. Beauchemin, Studies on Difficult Intramolecular Hydroaminations in the Context of Four Syntheses of Alkaloid Natural Products, The Journal of Organic Chemistry, 2013, 78, 24, 12735CrossRef