By D. J. Brown
Advent to the Pteridines.
basic Syntheses from Pyrimidines.
fundamental Syntheses from Pyrazines or different Heterocycles.
Pteridine and Its Alkyl and Aryl Derivatives.
Tautomeric Pteridinones and Extranuclear Hydroxypteridines.
Aloxypteridines, N-alkylpteridines, and Pteridine N-oxides.
The Sulfur-containing Pteridines.
Pteridine Amines and Imines.
Pteridinecarboxylic Acids and comparable Compounds.
Ionization and Spectra.
desk of easy Pteridines.
Chapter I advent to the Pteridines (pages 1–42):
Chapter II fundamental Syntheses from Pyrimidines (pages 43–141):
Chapter III basic Syntheses from Pyrazines or different Heterocycles (pages 143–163):
Chapter IV Pteridine and its Alkyl and Aryl Derivatives (pages 165–185):
Chapter V bankruptcy V. Halogenopteridines (pages 187–211):
Chapter VI Tautomeric Pteridinones and Extranuclear Hydroxypteridines (pages 213–289):
Chapter VII Alkoxypteridines, N?Alkylpteridinones, and Pteridine N?Oxides (pages 291–317):
Chapter VIII The Sulfer?Containing Pteridines (pages 319–341):
Chapter IX Pteridine Amines and Imines (pages 343–375):
Chapter X Pteridinecarboxylic Acids and similar Compounds (pages 377–414):
Chapter XI The Hydropteridines (pages 415–443):
Chapter XII Ionization and Spectra (pages 445–509):
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Extra info for Chemistry of Heterocyclic Compounds: Fused Pyrimidines Part III: Pteridines, Volume 24
E3(1)]. Both 2( 1H)-and 6(5H)-pteridinone undergo covalent hydration to give their 3,4- and 7,8-hydrate (73),respectively. The same substrates and many of their derivatives give similar adducts with alcohols, amines, acetone, sodium bisulfite, acetylacetone, diethyl malonate, and many other such reagents. Most of the adducts have been isolated and characterized. The 5,6-bond may also be with involved as in the reaction of 2-amino-7,8-dihydro-4(3H)-pteridinone mercaptoacetic acid to give the 5,6-adduct, 2-amino-6-carboxymethylthio5,6,7,8-tetrahydro-4(3H)-pteridinone (74) (Ch.
The oxidation of dihydropteridines usually arises when such compounds have been obtained by primary synthesis or by adduct formation from a less-substituted pteridine. For example, 3,4-dihydro-2pteridinamine (76), prepared by primary synthesis from a pyrazine, was oxidized to 2-pteridinamine by permanganate in pyridine. 6-Methyl-7,S-dihydro2,4(1H,3H)-pteridinedione (77), made by a Boon synthesis, gave 6-methyl2,4( 1H,3H)-pteridinedione on oxidation with hydrogen peroxide or permanganate. The covalent hydrate (78)of 2(1H)-pteridinone gave 2,4(1H,3H)-pteridinedione on prolonged aeration of an aqueous solution or by permanganate oxidation.
B(6)] This very common process is typified in the oxidation of this substrate (86)to 2-amino-4-oxo-3,4-dihydro-6-pteridinecarboxylic acid (88) by permanganate; ethyl or even quite complicated substituted-alkyl side chains are amenable to such oxidation but phenyl substituents are not. (d) Hydroxyalkyl to Formyl (Ch. VI, Sect. B) Such oxidations may be done with manganese dioxide, as in the conversion of 6-hydroxymethyl-4-methylthio-2-pteridinamine (89) into 2-amino-4-methylsulfonyl-6-pteridinecarbaldehyde (W), or with periodate, as in the transforminto 2-amino-4ation of 2-amino-6-a,B,y-trihydroxypropyl-4(3H)-pteridinone oxo-3,4-dihydro-6-pteridinecarbaldeh yde.
Chemistry of Heterocyclic Compounds: Fused Pyrimidines Part III: Pteridines, Volume 24 by D. J. Brown