N-N Bond Formation between Primary Amines and Nitrosos: Direct Synthesis of 2-Substituted Indazolones with Mechanistic Insights
Jie S. Zhu, Niklas Kraemer, Marina E. Shatskikh, Clarabella J. Li, Jung-Ho Son, Makhluf J. Haddadin, Dean J. Tantillo, Mark J. Kurth*
*Department of Chemistry, University of California Davis, 1 Shields Avenue, Davis, California 95616, United States, Email: mjkurthucdavis.edu
J. S. Zhu, N. Kraemer, M. E. Shatskikh, C. J. Li, J.-H. Son, M. H. Haddadin, D. J. Tantillo, M. J. Kurth, Org. Lett., 2018, 20, 4736-4739.
DOI: 10.1021/acs.orglett.8b01655 (free Supporting Information)
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The key step in a concise, one-step route to indazolones from primary alkyl amines and o-nitrobenzyl alcohols involves base-mediated in situ o-nitrobenzyl alcohol → o-nitrosobenzaldehyde conversion.
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J. S. Zhu, N. Kraemer, C. J. Li, M. J. Haddadin, M. J. Kurth, J. Org. Chem., 2018, 83, 15493-15498.