General Reference

Chemistry of Heterocyclic Compounds: The Pyrimidines, Volume by Desmond J. Brown

By Desmond J. Brown

Content material:
Chapter I advent to the Pyrimidines (pages 1–30):
Chapter II The important artificial technique (pages 31–81):
Chapter III different equipment of basic Synthesis (pages 82–115):
Chapter IV Pyrimidine and its C?Alkyl and C?Aryl Derivatives (pages 116–137):
Chapter V Nitro?, Nitroso?, and Arylazo?Pyrimidines (pages 138–161):
Chapter VI Halogenopyrimidines (pages 162–226):
Chapter VII Hydroxy? and Alkoxy?Pyrimidines (pages 227–271):
Chapter VIII Sulphur?Containing Pyrimidines (pages 272–305):
Chapter IX The Aminopyrimidines (pages 306–355):
Chapter X The N,?Alkylated Pyrimidines and Pyrimidine?N,?Oxides (pages 356–388):
Chapter XI The Pyrimidine Carboxylic Acids and similar Derivatives (pages 389–429):
Chapter XII The diminished Pyrimidines (pages 430–463):
Chapter XIII The Ionization and Absorption Spectra of Pyrimidines (pages 464–500):

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Extra resources for Chemistry of Heterocyclic Compounds: The Pyrimidines, Volume 16

Sample text

Further, by prior substitution of the methylene group of (I), a 5Me i /% We/%O (1) 0 -+ Me NH -& (11) (111) NH,/'\Ph M "Ph i2H,O substituted pyrimidine results. The amidine (11) may also be replaced by urea, thiourea, guanidine, or formamidine, and these yield a pyrim31 32 Chapter XI idine substituted in the 2-position by hydroxy, mercapto, amino, or without a group. When these reagents already carry an N-,0-, or S-alkyl group, N-substituted pyrimidines or 2-alkoxy or alkylthio derivatives are obtained.

SOC. chim. France, [Z], 31, 146 (1879). 9. , 17, 2519 (1884). 10. , 18, 759 (1885). 11. Widman, J . prakt. , PI, 38, 185 (1888). 12. von Meyer, Ber. K. sachs. Ges. Wiss. Math. Ibhys. ,5’7. 324 (1905). 13. , 32, 1525 (1899). 14. Johnson, J. I d . Eng. C h . , 10, 306 (1918). 15. , 59A, 158 (1926). 16. , 59A. 7 (1926). 17. , 59A, 11 (1926). 18. , 54, Sonderheft (1921). 19. Pringsheim. avagew. C k m . , 39,61 (1926). 20. asgezu. , 29, I, 189 (1916). 21. Vickery, Biographical Memoirs, Nat. Acad. Sci.

9). Degradative oxidation of pyrimidines, although it is occasionally informative, has been little used. Oxidative modification of groups differs little in principle from similar procedures in the benzene series. Thus a C-methyl- or styrylpyrimidine yields a carboxylic acid with permanganate, a hydroxymethyl group may be oxidized to an aldehyde or acid according to conditions, a mercapto group may be oxidized to a disulphide with iodine (but not by air, except in the 5-position), and this in turn yields a sulphonic acid with hydrogen peroxide or permanganate.

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