Photochemical Preparation of 1,2-Dihydro-3H-indazol-3-ones in Aqueous Solvent at Room Temperature

Jie S. Zhu, Niklas Kraemer, Clarabella J. Li, Makhluf J. Haddadin, 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, C. J. Li, M. J. Haddadin, M. J. Kurth, J. Org. Chem., 2018, 83, 15493-15498.

DOI: 10.1021/acs.joc.8b02356

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Abstract

o-Nitrosobenzaldehyde is a useful reactive intermediate for the synthesis of nitrogen heterocycles. This intermediate can be photochemically generated in situ from o-nitrobenzyl alcohols in an efficient manner for the construction of 1,2-dihydro-3H-indazol-3-ones using an aqueous solvent at room temperature.

see article for more examples

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N-N Bond Formation between Primary Amines and Nitrosos: Direct Synthesis of 2-Substituted Indazolones with Mechanistic Insights

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.

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Key Words

indazolones, photochemistry

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ID: J42-Y2018