By Raymond N. Castle
Chapter I actual houses 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
Dimetallic salts of a few substituted maleic hydrazides have been reported, but they are unstable and difficult to prepare (116). 00 A few dielectric constants for pyridazinones and maleic hydrazides have been recorded (1 17-1 1S), and some fairly extensive polarographic studies have been undertaken (114, 119-122). Although many pyridazinones have been shown to have slight biological activity, only maleic hydrazide has been studied extensively. It was introduced as a plant growth regulator in 1949 (123), and numerous patents and papers covering its commercial production and use have appeared.
55). Substitution always occurs at the 4-position first, and any further replacements are sluggish (30). Alkoxy- and Aryloxypyridazines 55 In this connection it is of interest that alkoxy groups at the 4- (or 5 - ) position of pyridazines are transformed into better leaving groups than halogens at the 3- (or 6-) position by the activation of the ring. For example, treatment of 3,6-dichloro-4-methoxypyridazinewith alcoholic ammonia yields 4-amino-3,6-dichloropyridazine by replacement of the methoxy group (Eq.
49, 1139 (1968). 52. Adam, Grimison, and Rodriquez, J . Chem. , 50, 645 (1969). 53. Tokuhiro and Fraenkel, J. Amer. Chem. ,91, 5005 (1969). 54. Yonezawa, Kato, and Kato, Theor. Chim. Acta, 13, 125 (1969). 55. Yonezawa, Yamabe, and Kato, Bull. Chem. Soc. , 42, 76 (1969). 56. Schneider, J . Amer. Chem. , 70, 627 (1948). 57. Lowdin, J. Chem. , 19, 1323 (1951). 58. Orgel, Cottrell, Dick, and Sutton, Trans. , 47, 113 (1951). 59. Amos and Hall, Mol. , 4, 25 (1961). 60. Hiickel and Jahnentz, Chem. , 75B, 1438 (1942).
Chemistry of Heterocyclic Compounds: Pyridazines, Volume 28 by Raymond N. Castle