By Raymond N. Castle
Chapter I actual homes of Pyridazines (pages 1–22): Anne G. Lenhert and Raymond N. Castle
Chapter II The Pyridazinones, Alkoxy? and Aryloxy?Pyridazines, and comparable Compounds (pages 23–218): James W. Mason and Duane L. Aldous
Chapter III Halopyridazines (pages 219–352): Duane L. Aldous and Raymond N. Castle
Chapter IV Pyridazine Aldehydes, Ketones, and Alcohols (pages 353–406): Anne G. Lenhert and Raymond N. Castle
Chapter V Pyridazinecarboxylic Acids (pages 407–461): James W. Mason
Chapter VI Aminopyridazines (pages 463–627): Takenari Nakagome
Chapter VII Nitropyridazines and Their aid items (Except Amines) (pages 629–673): Takenari Nakagome
Chapter VIII Pyridazine N?Oxides (pages 675–753): Takanobu Itai
Chapter IX Sulfur Compounds of Pyridazines (pages 755–837): M. Tisler and B. Stanovnik
Read Online or Download Chemistry of Heterocyclic Compounds: Pyridazines, Volume 28 PDF
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Additional resources for Chemistry of Heterocyclic Compounds: Pyridazines, Volume 28
For example, treatment of succinhydrazide with phosphoryl bromide yields 3,6-dibromopyridazine (Eq. 35) (182). H I H (35) Br 'Br Although they do not normally react-as ketone carbonyl groups, the 0x0 functions of both reduced and fully aromatic pyridazinones can be replaced by aromatic Grignard reagents. Reduced pyridazinones react by 1,2-addition, and apparently form diaryldihydropyridazines which dehydrogenate spontaneously. Only the fully aromatized products could be isolated (Eq. 36) (183-1 85).
38, 1508 (1963). 92. Favini, Vandoni and Simonetta, Theor. Chim. Acta, 3, 45 (1965). 93. Perkins, J. Mol. , 22, 464 (1967). 94. Dodd, Hopton and Hush, Proc. Chem. , 61 (1962). 95. Parkin and Innes, J. Mol. , 15, 407 (1965). 96. Hochstrasse and Marzzaco, J . Chem. , 46, 4155 (1967). 97. Hochstrasse and Marzzacco, J . Chem. , 49, 971 (1968). 98. R. Acad. , Paris, 261,4693 (1965). 99. Iwaizumi and Azumi, Nippon Kagaku Zasshi, 84, 694 (1963); Chem. , 60, 122 (1964). 100. , B28, 4524 (1968); Chem.
In at least one case, a pyridazinone has been converted to its hydrazone. Thus 1 -methyl-6(1H)pyridazinone was treated with formylhydrazine and triethyloxonium fluoroborate to yield the 6-hydrazone (Eq. 38) (127). The hydrazone is reported to undergo oxidative coupling to yield azo dyes. Oximes 45 Reactions of several 4(1H)pyridazinones have also been reported (79), but these were formed by cyclization of the ring rather than replacement of the pyridazinone oxygen function. CHs CH3 B. Reactions of the Nucleus 1 , Electrophilic Substitution Pyridazinones do not undergo electrophilic substitution readily, but several instances of such reactions have been reported.