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Updated: May 5, 2026

Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives
Published on: January 19, 2016
C-H functionalization directed by transformable nitrogen heterocycles: synthesis of ortho-oxygenated arylnaphthalenes
Shiva K Rastogi1, Derek C Medellin, Alexander Kornienko
1Department of Chemistry and Biochemistry, Texas State University, San Marcos, TX 78666, USA. a_k76@txstate.edu.
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.
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