One-Pot Synthesis of Phthalazines and Pyridazino-aromatics: A Novel Strategy for Substituted Naphthalenes
Simon N. Kessler and Hermann A. Wegner*
*Department of Chemistry, University of Basel, St. Johanns-Ring 19, 4056 Basel, Switzerland, Email: hermann.wegnerunibas.ch
S. N. Kessler, H. A. Wegner, Org. Lett., 2012, 14, 3268-3271.
DOI: 10.1021/ol301167q (free Supporting Information)
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A one-pot strategy allows the synthesis of phthalazines and pyridazino-aromatics starting from aromatic aldehydes. A variety of substituents ranging from electron withdrawing to donating is tolerated furnishing the desired 1,2-diazine in good to excellent yields. A subsequent bidentate Lewis acid catalyzed inverse electron-demand Diels-Alder (IEDDA) reaction opens a novel two-step entry into substituted naphthalenes, such as Naproxen.
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proposed reaction pathway