ISBN-10: 0470186887

ISBN-13: 9780470186886

ISBN-10: 0471382051

ISBN-13: 9780471382058

Content material:
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 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

Sample text

61. , Katritzky, Academic Press, New York, 1963, Vol. 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.

No attempt has been made to place these reactions in systematic order other than that of degree of utility, and no general mechanistic system is foIIowed. a. Innlerchange of Halogen Atoms (Ch. V, Sects. IGb and 1F) Such interchanges are sometimes necessary in order to provide a more reactive halogen than the one in situ. Only a restricted number of examples are known. Thus chloropurines treated with silver fluoride in high boiling solvents give the analogous fluoropurines. A specific route for 6-fluoropurines involves conversion of the 6-chloro analogue to the trimethylammonium quaternary chloride and reacting this with an alkali metal fluoride.

Under these conditions adenine exhibits a single wave but a tetrahydro derivative results, passing through the 1,6-dihydro stage during which the C,,-amino group is lost. Hypoxanthine shows only weak waves although reduction to dihydro derivative occurs, whereas guanine is not reduced under these conditions. Polarographic studies of 2,6-diaminopurine58and 6 - t h i o p ~ r i n have e ~ ~ been made. 6o F. Solubility and Melting Point Purine and its C-alkyl analogues show a high water solubility (purine 1 in 2 at 20”).

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