By John H.; Wiley; Lister, John Henry; John Wiley & Sons Wiley-Interscience Lister
Creation to the Purines (H1).
Synthesis from Pyrimidines.
Purines Syntheses from Imidazoles and different Precursors (H 91).
Purine and C -Alkyl, C -Aryl and N -Alkyl Derivatives (H 117).
Halogenopurines (H 135).
Oxo-(Hydroxy-) and Alkoxypurines (H 203).
Thioxo- and Selenoxopurines and Derivatives (H 269).
The Amino (and Amino-Oxo) Purines (H 309).
The Purine Carboxylic Acids and similar Derivatives (H 367).
Nitro-, Nitroso-, and Arylazopurines (H 401).
Purine-N -Oxides (H 409).
The decreased Purines (H 427).
Enlarged Purine-Containing constructions (New).
The Spectra of Purines (H 507).
Systematic Tables of easy Purines.
Chapter I advent to the Purines (H1) (pages 1–20):
Chapter II Synthesis from Pyrimidines (pages 21–60):
Chapter III Purines Syntheses from Imidazoles and different Precursors (H91) (pages 61–82):
Chapter IV Purine and C?Alkyl, C?Aryl, and N?Alkyl Derivatives (H117) (pages 83–98):
Chapter V Halogenopurines (H135) (pages 99–132):
Chapter VI Oxo?(Hydroxy?) and Alkoxypurines (H203) (pages 133–178):
Chapter VII Thioxo? and Selenoxopurines and Derivatives (H269) (pages 179–212):
Chapter VIII The Amino (and Amino?Oxo)Purines (H309) (pages 213–282):
Chapter IX The Purine Carboxylic Acids and similar Derivatives (H367) (pages 283–302):
Chapter X Nitro?, Nitroso?, and Arylazopurines (H401) (pages 303–306):
Chapter XI Purine?N?Oxides (H409) (pages 307–324):
Chapter XII The lowered Purines (H427) (pages 325–336):
Chapter XIII Enlarged Purine?Containing constructions (New) (pages 337–346):
Chapter XIV The Spectra of Purines (H507) (pages 347–384):
Chapter XV Systematic Tables of easy Purines (pages 385–424):
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Additional resources for Chemistry of Heterocyclic Compounds: The Purines, Supplement 1, Volume 54
S H Me 56 57 Me 58 M. Cyclization with Urea (H59) This continues to be the most favored route for 8-oxopurine formation which, in spite of the forcing conditions employed, generally affords satisfactory to good yields. 25 h) in 70-90'Yo yields. 5 h) is not surprising since the 9-benzyl analog which has been similarly preparedls5also exhibits a deactivated halogen attributed to the presence of the 8-0x0 group. N. Cyclizationwith Thiourea ( H a ) Current literature still contains many examples of this well-tried and tested route to 8-thioxopurines.
0. Cyclization with Cyanates. lsocyanates and Derivatives (H61) . . . . . . P. Cyclization with lsothiocyanates (H62) . . . . . . . . . . . . . R . Cyclization with Carbon Disulfide (H64) . . . . . . . . . . . . S. Cyclization with Phosgene(H67) . . . . . . . . . . . . . . U . Cyclization with Chlorocarbonic Ester (H68) . . . . . . . . . . . V . Cyclizaiion with Aldehydes and Ketones (H69) . . . . . . . .
Under these conditions hydrolysis of the methylthio group to thioxo followed by oxidation to the disulfide seems most likely. ”~ for the removal of elements of water, but when this reagent was reacted with 4,6bis(3-N-methylureido)-5-formamidopyrimide (8)the product was not the expected 9-carbamoyl derivative (9) but the 9-unsubstituted purine (10). B. *3yExtended Traube* reactions are reported in which the 8-hydroxy group of uric acid derivatives is replaced by hydrogen on heating with a formic acid-trimethylamine mixture.