Chapter I creation 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 similar Derivatives (pages 367–399):
Chapter X Nitro?, Nitroso?, and Arylazopurines (pages 401–408):
Chapter XI Purine?N?Oxides (pages 409–426):
Chapter XII The diminished 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
Oxidation of extranuclear groups parallels that found with the benzene analogues, thio groups being converted to sulphinic and sulphonic acid groups by hydrogen peroxide or permanganate solution, while if carried out in the presence of ammonia solution sulphamoyl groups result. Iodine has been used to convert thiopurines to their dipurinyl disufphide derivatives. Modified methyl groups are oxidised to their aldehyde and carboxyl forms. A C,,,propenyl group can be removed by oxidative hydrolysis using permanganate.
Zinc dust and dilute acid will also give deoxypurines but the severity of the conditions is such as to lead to ring degradation in many cases. b. Removal of Groups Halogeno, thio, and alkylthio groups are removed under reducing conditions. Hydrogenolysis is the agent of choice for halogenopurines, a paIIadium catalyst being employed in the presence of a base, such as magnesium oxide, to remove hydrogen halides produced, the latter being conducive to nuclear reduction. Mono-, di-, and trichloropurines have been reduced to purine by stepwise removal of the chlorine atoms in this manner.
I, p. 177. 41. 42. 43. 44. 45. 46. 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.
Chemistry of Heterocyclic Compounds: Fused Pyrimidines, Part II: Purines, Volume 24