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

Organic & Biomolecular Chemistry Pub Date: 2013-11-22 DOI: 10.1039/C3OB42255K

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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