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Issue 3, 2014
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C–H functionalization directed by transformable nitrogen heterocycles: synthesis of ortho-oxygenated arylnaphthalenes from arylphthalazines

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Abstract

Two protocols for oxygenation of aromatic C–H bonds ortho-positioned to the phthalazine ring were developed. The transannulation of the phthalazine ring to a naphthalene moiety by an Inverse Electron Demand Diels–Alder (IEDDA) reaction led to the synthesis of naphtho[2,1-c]chromenes, 1-(ortho-hydroxyaryl)naphthalenes and 6,7-dihydrobenzo[b]naphtho[1,2-d]oxepine. This new strategy based on the utilization of transformable nitrogen heterocycles in C–H functionalization chemistry can be potentially applicable to the synthesis of a broad range of biaryl compounds.

Graphical abstract: C–H functionalization directed by transformable nitrogen heterocycles: synthesis of ortho-oxygenated arylnaphthalenes from arylphthalazines

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Publication details

The article was received on 13 Nov 2013, accepted on 20 Nov 2013 and first published on 22 Nov 2013


Article type: Communication
DOI: 10.1039/C3OB42255K
Citation: Org. Biomol. Chem., 2014,12, 410-413
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    C–H functionalization directed by transformable nitrogen heterocycles: synthesis of ortho-oxygenated arylnaphthalenes from arylphthalazines

    S. K. Rastogi, D. C. Medellin and A. Kornienko, Org. Biomol. Chem., 2014, 12, 410
    DOI: 10.1039/C3OB42255K

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