Download Chemistry of Heterocyclic Compounds: The Pyrimidines, Volume by Desmond J. Brown, R. F. Evans, M. D. Fenn PDF

By Desmond J. Brown, R. F. Evans, M. D. Fenn

Fundamental Syntheses.

The crucial Synthesis.

Pyrimidine, Alkylpyrimidines, and Arylpyrimidines.

Nitro-, Nitroso-, and Arylazopyrimidines.





Pyrimidinecarboxylic Acids and similar Derivatives.

The diminished Pyrimidines.

The Ionization and Spectra of Pyrimidines.



topic Index.Content:
Chapter 1 creation to Pyrimidine Chemistry (pages 1–47):
Chapter 2 fundamental Syntheses (pages 49–148):
Chapter three The imperative Synthesis (pages 149–239):
Chapter four Pyrimidine, Alkylpyrimidines, and Arylpyrimidines (pages 241–281):
Chapter five Nitro?, Nitroso?, and Arylazopyrimidines (pages 283–328):
Chapter 6 Halogenopyrimidines (pages 329–437):
Chapter 7 Oxypyrimidines (pages 439–551):
Chapter eight Thiopyrtmidines (pages 553–609):
Chapter nine Aminopyrimidines (pages 611–682):
Chapter 10 Pyrimidinecarboxylic Acids and similar Derivatives (pages 683–735):
Chapter eleven The lowered Pyrimidines (pages 737–821):
Chapter 12 The Ionization and Spectra of Pyrimidines (pages 823–870):

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Additional info for Chemistry of Heterocyclic Compounds: The Pyrimidines, Volume 52

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Acylation and alkylation. Acylation of a tautomeric pyrimidinone may give an 0- or N-acylated product or a mixture of both. In contrast, alkylation usually gives an N-alkylpyrimidinone with perhaps a trace of alkoxypyrimidine; diazomethane tends to afford more 0-alkylated product than do most other reagents: for example, 2(1H)-pyrimidinone (93) so gives 2-methoxypyrimidine (94) (1 7%) and l-methyl-2(1H)-pyrimidinone (95) (52%). Aminolysis. Although most conversions of pyrimidinones into pyrimidinamines are done indirectly via chloropyrimidines or pyrimidinethiones, a direct route is available providing that the substrate and product are both sufficiently stable to withstand the vigorous conditions.

Selective aminolysis of a di- or trihalogenopyrimidine can be very useful: for example, 2,4-dichloro-5-nitropyrimidine(77) with ice-cold aqueous ammonia gives virtually pure 2-chloro-5-nitro-4-pyrimidinamine (78), an extremely versatile intermediate. , 79);conditions must be gentle in order to avoid loss of methyl halide to give the dimethylaminopyrimidine (80). 5-Halogenopyrimidines undergo regular or cine aminolyses under relatively vigorous conditions. 71 78 19 80 Hydrolysis and alcoholysis.

9. 3) The tautomeric pyrimidinethiones are much more reactive than are their oxygen analogs, and hence of much wider use as intermediates. Desulfurization. The removal of sulfur from pyrimidinethiones in favor of hydrogen may be done reductively, usually by stirring with Raney-nickel catalyst (3-5 parts) in boiling water, aqueous ammonia, or ethanol. The procedure is exemplified in the conversion of 4-isopropyl-6-methyl-2( 1H ) pyrimidinethione into 4-isopropyl-6-methylpyrimidine or of 5,6-diamino2,4( lH,3H)-pyrimidinedithione (1 13) into 4,5-pyrimidinediamine (114).

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