Chapter I advent to the Purines (pages 1–30):
Chapter II Syntheses from Pyrimidines (pages 31–90):
Chapter III Purine Syntheses from Imidazoles and different Precursors (pages 91–115):
Chapter IV Purine and the C?Alkyl and C?Aryl Derivatives (pages 117–134):
Chapter V Halogenopurines (pages 135–201):
Chapter VI The Oxo?(Hydroxy?) and Alkoxypurines (pages 203–267):
Chapter VII Thiopurines and Derivatives (pages 269–307):
Chapter VIII The Amino (and Amino?Oxo) Purines (pages 309–365):
Chapter IX The Purine Carboxylic Acids and comparable Derivatives (pages 367–399):
Chapter X Nitro?, Nitroso?, and Arylazopurines (pages 401–408):
Chapter XI Purine?N?Oxides (pages 409–426):
Chapter XII The lowered Purines (pages 427–437):
Chapter XIII The Spectra of Purines (pages 439–528):
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Additional info for Chemistry of Heterocyclic Compounds: Fused Pyrimidines, Part II: Purines, Volume 24
47. H. Lister Copyright 0 1971 by John Wiley & Sons, Ltd. CHAPTER II Syntheses from Pyrimidines Of the many purines synthesised to date the majority has been derived from pyrimidine precursors. These fall into three classes which in order of importance and utility are the derivatives of 4,5-diamino-, 5-amino-40x0-, and 4,5dioxopyrimidines. Because of the extensive use made of Traube-type condensations pyrimidines of the first class have had, by far, the greatest application to purine syntheses.
Important section of purine chemistry. A. Electrophilic Substitution Under this heading electrophilic displacement at both carbon and nitrogen atoms will be included. 10 Chapter I a. Nitration (Ch. X,Sect. 1Aa) This necessitates the presence of a strongly nucleophilic carbon atom at the 8-position. So far only N-methylated derivatives of xanthine appear to satisfy this requirement although, theoretically, any purine with a number of strong electron-donating groups should do so. 8-Nitroxanthines can also arise from electrophilic substitution of an 8-thio group by nitronium ion.
Me OH I E. Modification of Substitueats Under this heading are grouped various reactions which modify a group without rearrangement or fission of the bond joining it to the nucleus. 20 Chapter I a. Amino Groups (Ch. NHa) rather than the imino (:NH) form. Chemical behaviour is not, however, consistent with that of an aromatic amine, the nearest approach to such character being shown by 8-aminopurines. The lack of reactivity of amino groups at the 2- and 6-positions is best explained by considering them as components of cyclic guanidine and amidine systems, respectively.
Chemistry of Heterocyclic Compounds: Fused Pyrimidines, Part II: Purines, Volume 24