Chemistry of Heterocyclic Compounds: The Pyrimidines, Volume by Desmond J. Brown, R. F. Evans, M. D. Fenn
By Desmond J. Brown, R. F. Evans, M. D. Fenn
The imperative Synthesis.
Pyrimidine, Alkylpyrimidines, and Arylpyrimidines.
Nitro-, Nitroso-, and Arylazopyrimidines.
Pyrimidinecarboxylic Acids and comparable Derivatives.
The lowered Pyrimidines.
The Ionization and Spectra of Pyrimidines.
Chapter 1 creation to Pyrimidine Chemistry (pages 1–47):
Chapter 2 fundamental Syntheses (pages 49–148):
Chapter three The central 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 comparable Derivatives (pages 683–735):
Chapter eleven The diminished Pyrimidines (pages 737–821):
Chapter 12 The Ionization and Spectra of Pyrimidines (pages 823–870):
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Extra resources for Chemistry of Heterocyclic Compounds: The Pyrimidines, Volume 52
Acidic or alkaline conditions may be used for the hydrolysis of pyrimidinamines: for example, 2-methylaminopyrimidine (154, R = Me) or 2-pyrimidinamine (154, R = H) gives 2(1H)-pyrimidinone (155) (HCI at 160" or 154 155 36 Introduction to Pyrimidine Chemistry NaOH at 1 lo", respectively); and 5-ethylamino-4-pyrimidinaminegives 5hydroxy-4(3H)-pyrimidinone (HCl at 100'). An alternative (indirect) procedure, involving treatment with nitrous acid, is applicable only to primary amines: for example, 4,6-dimethyl-2-pyrimidinaminegives 4,6-dimethyl-2(1H)-pyrimidinone (HNO,, AcOH) and Spyrimidinamine gives 5-pyrimidinol.
Alkylthiopyrimidines can undergo thiolysis to their usual precursors, pyrimidinethiones: although seldom used, the reaction is illustrated by the conversion of 6-amino-3-methyl-2-methylthiointo 6-amino-3-methyl-2thioxo- 1,2-dihydro-4(3H)-pyrimidinone(136) by heating with aqueous sodium hydrogen sulfide. Such transformations can be done also by thiation with phosphorus pentasulfide (mechanism unresolved) or by splitting the thioether with dry hydrogen chloride, aluminum chloride, hydriodic acid, or similar.
1 to facilitate an understanding of many original papers in which they occur. 3. FACTORS IN THE UNIQUITY OF PYRIMIDINE CHEMISTRY The unique reactions and properties of pyrimidine and its derivatives are derived from their electronic structures, which in turn result from five simple structural factors. It is surprising how often such factors can be used to explain, or even predict, the most diverse experimental observations. 1. The Activated 2- and 4/6-Positions The starred 2-, 4-, and 6-positions of pyrimidine (15) are naturally deficient in n-electrons by virtue of the powerful electron localization at the ring-nitrogen atoms.