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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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Abstract

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



Key Words

phthalazines, Directed Ortho Metalation


ID: J54-Y2012-2110