General Reference

Chemistry of Heterocyclic Compounds: Pyridazine and Pyrazine by J. C. Simpson

By J. C. Simpson

Content material:
Chapter I basic creation to Cinnoline Derivatives. instruction and houses of Cinnoline (pages 1–5):
Chapter II 4?Aryl?, 4?Acyl?, and 4?Carboxy?Cinnolines (pages 6–12):
Chapter III 4?Methylcinnolines (pages 13–15):
Chapter IV 4?Hydroxycinnolines (pages 16–28):
Chapter V 4?Chloro?, 4?Alkoxy?, and 4?Phenoxycinnolines (pages 29–34):
Chapter VI 4?Aminocinnolines (pages 35–38):
Chapter VII Cinnoline Quaternary Salts (pages 39–45):
Chapter VIII decreased Cinnolines (pages 46–51):
Chapter IX Cinnolines Containing extra Fused jewelry (pages 52–65):
Chapter X Phthalazines Unsubstituted within the Hetero Ring (pages 67–71):
Chapter XI 1?Alkyl?, 1?Aryl?, and 1,4?Diarylphthalazines (pages 72–77):
Chapter XII 1?Hydroxyphthalazines (pages 78–83):
Chapter XIII Alkyl, Aryl, and Acyl Derivatives of 4?(1?)Hydroxyphthalazines (pages 84–105):
Chapter XIV 1?Hydroxy?3?Aryl?3,4?Dihydrophthalazine?4?Acetic Acids (pages 106–118):
Chapter XV 3?Aryl?1?Ketophthalazines (pages 119–129):
Chapter XVI Methylated Derivatives of 3?Aryl?1?Ketophthalazines (pages 130–139):
Chapter XVII 1,4?Dihydroxyphthalazines (pages 140–156):
Chapter XVIII Monoalkyl and Monoacyl Derivatives of 1,4?Dihydroxyphthalazines (pages 157–167):
Chapter XIX Dialkyl and Diacyl Derivatives of 1,4?Dihydroxyphthalazines (pages 168–177):
Chapter XX 1?Halogeno? and 1,4?Dihalogenophathalazines (pages 178–182):
Chapter XXI 1?Aminophthalazines (pages 183–185):
Chapter XXII lowered Phthalazines (pages 186–190):
Chapter XXIII Condensed Phthalazines and Azaphthalazines (pages 191–200):
Chapter XXIV instruction of Quinoxalines from basic fragrant O?Diamines and 1,2?Dicarbonyl Compounds (pages 201–227):
Chapter XXV Quinoxalines Unsubstituted within the Hetero Ring (pages 228–231):
Chapter XXVI Quinoxaline N?Oxides (pages 232–234):
Chapter XXVII 2?Hydroxy? and 2,3?Dihydroxyquinoxalines (pages 235–245):
Chapter XXVIII Quinoxaline?2?Aldehydes (pages 246–249):
Chapter XXIX Quinoxaline?2?Carboxylic and ?2,3?Dicarboxylic Acids (pages 250–257):
Chapter XXX 2?Chloro? and 2,3?Dichloroquinoxalines (pages 258–262):
Chapter XXXI 2?Amino? and 2,3?Diaminoquinoxalines (pages 263–269):
Chapter XXXII 2?Alkoxy?, 2,3?Dialkoxy?, and 2,3?Diaryloxyquinoxalines (pages 270–272):
Chapter XXXIII 2?Methyl? and 2,3?Dimethylquinoxalines (pages 273–285):
Chapter XXXIV Quinoxaline Quaternary Salts (pages 286–292):
Chapter XXXV Formation of Quinoxalines from Compounds Containing a Furan Ring (pages 293–299):
Chapter XXXVI 2?Polyhydroxyalkaylquinoxalines (pages 300–309):
Chapter XXXVII decreased Quinoxalines (pages 310–331):
Chapter XXXVIII Condensed Quinoxalines (pages 332–355):
Chapter XXXIX Azaquinoxalines (pages 356–357):

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Extra resources for Chemistry of Heterocyclic Compounds: Pyridazine and Pyrazine Rings: (Cinnolines, Phthalazines, and Quinoxalines), Volume 5

Sample text

Chem. ,1949, 13G7. 32. Schofirld, J . Chem. 2408. Chemistry of Heterocyclic Compounds, Volume5 J. C. E. Simpson Copyright 0 1953 by Interscience Publishers, Inc. CHAPTER V 4-Chloro-, 4-Alkoxy-,and 4-Phenoxycinnolines 1. 4-Chlorocinnolines A. Preparation. '~usually a t looo. Normally the reaction is straightforward, and the products are isolated by dilution with ice water and basification, but Busch and Klett' observed that, in the preparation of 4chlorocinnoline itself, a black byproduct is formed when the diluted reaction medium is made alkaline.

P. 170". p. 114". These triasaphenanthrene derivatives are considered to arise by fission of the dihydropyridine ring of (XIX) and subsequent recyclization; however, their structures are not proved. WII) A somewhat unexpected property of the pyridylcinnoline (XX) is its susceptibility to oxidation. It is rapidly attacked by cold aqueous permanganate, giving a good yield of a single product of formula C1pH~OsNI. p. p. 172-174"), crystallizes from et,hylacetate in orange-red prisms, but from water aa a mixture of white and red needles; it shows marked amphoteric properties and dissolves in cold aqueous sodium bicarbonate.

Normally the reaction is straightforward, and the products are isolated by dilution with ice water and basification, but Busch and Klett' observed that, in the preparation of 4chlorocinnoline itself, a black byproduct is formed when the diluted reaction medium is made alkaline. This behavior is confirmed by Leonard and Boyd6 both in this reaction and also in the preparation of 4-chloro-6-bromocinnoline. but these authors find t h a t the extent of the side reaction with 4chlorocinnoline can be diminished by careful neutralization, instead of basification, of the acid solution.

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