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Chemistry of Heterocyclic Compounds: Acridines, Volume 9,

Content material:
Chapter I Acridines (pages 9–108): N. R. Raulins
Chapter II Aminoacridines (pages 109–140): B. Adcock
Chapter III 9?Acridanones (pages 141–377): J. M. F. Gagan
Chapter IV The Acridine Alkaloids (pages 379–432): J. E. Saxton
Chapter V Acridinium Salts and lowered Acridines (pages 433–517): I. A. Selby
Chapter VI Biacridines (pages 519–528): Frank Mccapra
Chapter VII Benzacridines and Condensed Acridines (pages 529–577): D. A. Robinson
Chapter VIII Acridine Dyes (pages 579–613): B. D. Tilak and N. R. Ayyangar
Chapter IX Chemiluminescent Reactions of Acridines (pages 615–630): Frank Mccapra
Chapter X Ultraviolet and visual Absorption Spectra (pages 631–664): Margaret L. Bailey
Chapter XI The Infrared Spectra of Acridines (pages 665–685): R. M. Acheson
Chapter XII The Nuclear Magnetic Resonance Spectra of Acridines (pages 687–707): R. M. Acheson
Chapter XIII The Mass Spectra of Acridines (pages 709–721): R. G. Bolton
Chapter XIV The interplay of Acridines with Nucleic Acids (pages 723–757): A. R. Peacocke
Chapter XV Acridines and Enzymes (pages 759–787): B. H. Nicholson
Chapter XVI The Antibacterial motion of Acridines (pages 789–813): A. C. R. Dean
Chapter XVII Carcinogenic and Anticarcinogenic homes of Acridines (pages 815–828): David B. Clayson
Chapter XVIII Acridine Antimalarials (pages 829–850): David W. Henry

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Extra resources for Chemistry of Heterocyclic Compounds: Acridines, Volume 9, Second Edition

Example text

208 The first-formed anil, 53 (R = -C6H4N(Me)2), when boiled with aniline in ethanol, loses nitrous acid to yield 54. This last compound on heating with acetic acid cyclizes to the acridine 55, with the loss of p-aminodimethylaniline. 53 54 55 50 Acridines F. Other Methods of Preparing Acridines It is difficult to categorize completely all acridine syntheses in terms of starting materials, reaction conditions, or products formed. All of those that can be described as related to phosphorus oxychloride cyclizations of diphenylamine-2-carboxylic acids, which were prepared in the Ullmann reaction, are considered in Chapter 111.

5-54 159 176 116 81 59 69-70 66-68 350 - 4-Methyl4-Methyl- 4-Hydroxy3-Hydroxy- - - 3-Hydroxy- - - - - - 2-Methyl- (Table Continued) Formic acid Chloroform Acetic acid Acetic acid Acetic anyhdride 2-Hydroxybenzoic acid 3-Hydroxybenzoic acid 4-Hydroxybenzoic acid Benzoic acid Benzoic acid 148 148 117 153 133 152 152 152 129 118 Acetic acid 156 2,4-Dimethylbenzoic acid 149 2,5-Dimethylbenzoic acid 149 Propionic acid 150,157 2-Ethylbutyric acid 140 Octanoic acid 140 Stearic acid 151 Stearic acida 121 4-Hydroxybenzoic acid 119 h, 9-Phenyl-3-phenylamino-b 3-Phenylamino- b 9-[3-(pMethylphenyl)propyll2-Methyl-9-phenyl9-Met hy l-3-phenylamino-b -9-Pelargonic acid 9-Pentadecyl9-Phenyl- 9-(2-Methylphenyl)9 4 3-Methylpheny1)944-Methylpheny1)- Acridine TABLE 11.

NH, groups). 7 E , 79 Aeration of a hot, finely divided suspension of an acridan in aqueous alkali, such as that obtained after a sodium amalgam reduction, will cause oxidation to the acridine, provided that the original acridan does not contain electronattracting groups. Substituents of this sort prevent oxidation by air, which is facilitated by amino and hydrexy grcup:. E0 Ferric chloride was first used in 1896 for the oxidation of 3,6-bisdimethylaminoacridan to the corresponding acridineE1; it has since been employed successfully for the oxidation of many 82-84 and other acridans.

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