Download Chemistry of Heterocyclic Compounds: Pyridazines, Volume 28 by Raymond N. Castle PDF

By Raymond N. Castle

Content material:
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

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Extra resources for Chemistry of Heterocyclic Compounds: Pyridazines, Volume 28

Example text

H H I CHpCOOCZHj I ClCHZCOOCrHj (3 1) CHACOOCZHj Pyridazinones (148, 149), pyridazinethiones (1 50), maleic hydrazides (139, 151, 152), and succinhydrazide (153) undergo Michael-like additions with activated olefins. Only N-substitution has been observed (139). Maleic hydrazides yield the monosubstituted products exclusively. This is in contrast to succinhydrazide which yields mono- and disubstituted products (153). Good yields are obtained with acrylate esters, acrylonitrile, and methyl vinyl ketone, while dihydrofuran, dihydropyran, and dihydrothiopyran give poor yields.

OCH, OCH, Reactions 51 Lithium aluminum hydride has also been used to reduce 4,5-dihydropyridazinones. However, this reagent attacks the cyclic amide moiety and removes the carbonyl oxygen while leaving the ring structure intact (Eq. 50) (218, 219). 4. Miscellaneous Ring Reactions There have been several reports of ring contraction reactions occurring in l-aryl-6(1H)pyridazinones (Eq. 51) (53, 189, 207, 220). Pyrazole products were always reported, but their substituents were effected by the conditions employed in the reaction.

90. El Sayed and Robinson, J. Chem. , 34, 1840 (1961). 91. Kearns and El-Bayoumi, J . Chem. , 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.

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