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 decreased 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 houses of Acridines (pages 815–828): David B. Clayson
Chapter XVIII Acridine Antimalarials (pages 829–850): David W. Henry
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Additional info for Chemistry of Heterocyclic Compounds: Acridines, Volume 9, Second Edition
237Rieche and M ~ e l l e have r ~ ~prepared ~ methylacridines by passing the vapors of aromatic amines, diluted with nitrogen, over aluminum oxide at 440": o-toluidine -+ 10% yield of 4 3 dimethylacridine; p-toluidine --+ 10% of 2,7-dimethylacridine; p-xylidine --+ 1,4,5,8-tetramethylacridine(63). 53 2 . ~*l Phloroglucinol and 2-aminobenzaldehyde, in an almost complementary reaction, were found to give 1,3-dihydroxyacridine in the presence of sodium hyd r o ~ i d e . * This ~ * reaction was fully investigated later,243the reactants being allowed to stand in aqueous solution at room temperature for 5 days at definite pH values, 4-13.
Methods of Preparation of Acridines 51 More recent applications of selenium dehydrogenation of perhydroacridines222 and tetrahydroa~ridine22~ have been reported, but there is no indication that yields of acridines are improved. 221Yields of 5 to 17% of acridine have been obtained when tetra- and octa-hydroacridines were heated in boiling xylene with 5-10y0 excess of c h l 0 r a n i 1 . j ~~ used chloranil in the dehydrogenation of diethyl acridan-9-phosphonate. Decarboxylation and distillation with lead dioxidezz6has transformed appropriately substituted 1,2,3,4-tetrahydroacridine-9-carboxylic acids into 2- and 3-methylacridine ; this reagent also aromatized some reduced benza c r i d i n e ~Chloranil .
Frothing, due largely to the evolution of carbon dioxide, is eliminated, and the formation of oxanilides is precluded. 3 moles) and formic acid (1-2 moles), in sufficient glycerol to ensure homogeneity, to 155-175” for about an hour. 164A list of acridines prepared by this method is given in Table 111. 163 The mechanism of the reaction has been investigated in some The first stage is undoubtedly the production of 3-aminoformanilide (21). This compound was isolated when the reaction was not allowed to go to completion ; when treated with rn-phenylenediamine under the usual reaction conditions, it gave a larger yield of 3,6-diaminoacridine than could be obtained from formic acid and the diamine.