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Review | Regular issue | Vol 26, No. 2, 1987, pp.481-496
Published online, 1st January, 1970
DOI: 10.3987/R-1987-02-0481
Advances in the Synthesis of Substituted Pyridazines via Introduction of Carbon Functional Group into the Parent heterocycle

Gottfried Heinisch

*Institute of Pharmaceutical Chemistry, University of Vienna, Währinger Strasse 10, A-1090 Vienna, Austria

Abstract

Methods for the convenient synthesis of various simple pyridazine derivatives based on Minisci-type reactions are reviewed. Due to the pronounced regioselectivity of radicalic attack at C-4 and/or C-5 of the protonated 1,2-diazine system homolytic substitution reactions with nucleophilic carboncentered radicals permit an experimentally easy access to pyridazinecarbaldehydes and C-alkyl or C-alkoxycarbonyl derivatives thereof (via trioxanylpyridazines), alkyl and aryl pyridazinylketones (via acyl- or aroylpyridazinecarboxylic acids), pyridazinedicarboxylic acid esters, C-alkylpyridazine monocarboxylic acid esters and α-N-amidoalkylpyridazines. The reactivity and the synthetic utility of these classes of compounds are discussed briefly. In addition, syntheses of 3-pyridazinecarbonitrile and 4- or 6- alkyl derivatives thereof are described. These compounds are readily obtained via N-arylsulfonyl Reissert compounds.