Literature DB >> 30468072

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

Jie S Zhu1, Niklas Kraemer1, Clarabella J Li1, Makhluf J Haddadin2, Mark J Kurth1.   

Abstract

o-Nitrosobenzaldehyde is a reactive intermediate useful in the synthesis of nitrogen heterocycles. Previous strategies for using o-nitrosobenzaldehyde involve its isolation via chromatography and/or formation under harsh conditions. Herein, this intermediate was photochemically generated in situ from o-nitrobenzyl alcohols in a mild, efficient manner for the construction of 1,2-dihydro-3 H-indazol-3-ones using an aqueous solvent at room temperature. This convenient reaction offers several advantages over reported methods. The commercially available photoreactor employed 3 × 18 W bulbs outputting broad emission above 365 nm.

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Year:  2018        PMID： 30468072      PMCID： PMC6467708          DOI： 10.1021/acs.joc.8b02356

Source DB:  PubMed          Journal:  J Org Chem        ISSN： 0022-3263            Impact factor:   4.354


  22 in total

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

Authors:  Jie S Zhu; Niklas Kraemer; Marina E Shatskikh; Clarabella J Li; Jung-Ho Son; Makhluf J Haddadin; Dean J Tantillo; Mark J Kurth
Journal:  Org Lett       Date:  2018-08-01       Impact factor: 6.005

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Review 6.  The Davis-Beirut Reaction: a novel entry into 2H-indazoles and indazolones. Recent biological activity of indazoles.

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3.  Davis-Beirut Reaction: A Photochemical Brønsted Acid Catalyzed Route to N-Aryl 2H-Indazoles.

Authors:  Niklas Kraemer; Clarabella J Li; Jie S Zhu; Julio M Larach; Ka Yi Tsui; Dean J Tantillo; Makhluf J Haddadin; Mark J Kurth
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4.  Accessing Multiple Classes of 2 H-Indazoles: Mechanistic Implications for the Cadogan and Davis-Beirut Reactions.

Authors:  Jie S Zhu; Clarabella J Li; Ka Yi Tsui; Niklas Kraemer; Jung-Ho Son; Makhluf J Haddadin; Dean J Tantillo; Mark J Kurth
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6.  Rapid and halide compatible synthesis of 2-N-substituted indazolone derivatives via photochemical cyclization in aqueous media.

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  7 in total

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