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 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
16 Chapter I e. Thio- (and Methylthio-) to Oxopurines (Ch. VI, Sect. IF) As in related heterocyclic systems, such as pyrimidines, thio groups in purines show reIuctance toward hydrolytic conversion to the 0x0 form. , nitric and nitrous acids) for this purpose are to be found but this approach has IittIe practical application as more productive procedures are available. Of the methods outlined below the first two have general application and the others a more limited scope. (a)Mild oxidising agents convert a thio group to the sulphinic or higher oxidised sulphonic acid form.
If akylation with chloroaceticacid, rather than an alkyl halide, is made the carboxymethylthiopurine produced can be very acid labile. (d) Miscellaneous strong oxidising agents, which include hydrogen peroxide, manganese dioxide, and nitric acid have been used to replace the sulphur atom by oxygen, but the likelihood that the sulphydryl group may be replaced by hydrogen under these conditions is aIways present. Scheme B (R = purinyl) summarises these conversions. RSOaH f t 1 RSH + RSCHoCOzH RSMe SCHEMEB ----f P RSOzOH ROH 1 RS0,Me f.
2). The analogous oxazolo[5,4-d]pyrimidines,from 6-oxopyrimidines, are not formed under the usual cyclising conditions but their isolation after the use of vigorous, strongly acid conditions has been made. If in addition interesting to note that the first example of pteridine formation arose from4 an attempted purine preparation. However, not all I ,2-dicarbonyl derivatives give pteridines, as examples exist in which only one of the carbonyl groups takes part in the reaction, and a purine is formed.