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Content material:
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 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 resources for Chemistry of Heterocyclic Compounds: Fused Pyrimidines, Part II: Purines, Volume 24

Sample text

The mechanisms involved in metatheses of this type have been the subject of a number of investigations from which a satisfactory theory to explain the reaction sequence has resulted. Chloropurines are the most versatile derivatives in which the order of replacement of the 2-, 6-, and 8-chlorine atoms by nucleophilic agents is governed by the ionic state existing at the time of reaction. With the anion of 2,6,8-trichloropurine attack by bases follows the order c(6), C(z,then C(8). The latter order of substitution also holds where the cation is involved, as with reactions carried out in acid media.

G . Thio- to Aminopurines (Ch. VII, Sect. 1Cf) The case of the replacement of methylthio by amino has been dealt with already (Sect. 4Bh), this being the general means by which a sulphur atom undergoes nucleophific displacement by an amine. The inertness shown by thio groups toward hydrolysis is reflected in a similar lack of activity toward amines. A number of cases of amination are known with N-methylated thiopurines, but the method is too limited to be of general applicability and is confined to replacement of 6-thio groups for which forcing conditions are required.

31, 542 (1898). 15, Traube. , 33, 1371 (1900). 16. , New York, 1931, Ch. 4. 17. Bendich, in The Nucleic Acids. , Chargaff and Davidson, Academic Press, New York, 1955, Vol. 1, Ch. 3. 18. , London, 1950, Vol. X, p, 274. 19. , Sir Robert Robinson, Pergamon Press, London, 1964. 20. , London, 1960, Yol. IVc, Ch. 20. 21. , Elderfield, Wiley, New York. 1967, Vol. VlII, Ch. 3. 22. Albert, Heterocyclic Chemistry, 2nd ed.. Athlone Press, London, 1968. 23. , Katritzky, Academic Press, New York, 1966, Vol.

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