Pyrimidines, Volume 16

Desmond J. Brown is Professor of Chemistry at The Australian National University's Research School of Chemistry.S. F. Mason, The University, Exeter, England.

• Chapter I. Introduction to the Pyrimidines 11. History 12. Nomenclature 33. The Unique Basis of Pyrimidine Chemistry 54. General Summary of Pyrimidine Chemistry 95. Physical Properties of Pyrimidines 26Chapter II. The Principal Synthetic Method 311. General Scope 312. Use of β –Dialdehydes 323. Use of β-Aldehydo Ketones 344. Use of β Diketones 365. Use of β-Aldehydo Esters 386. Use of β-Keto Esters 487. Use of β-Diesters (Malonic Esters) 518. Use of β-Aldehydo Nitriles 599. Use of β -Keto Nitriles 6510. Use of β -Ester Nitriles11. Use of β -Dinitriles (Malononitriles)Chapter III. Other Methods of Primary Synthesis 821. General Remarks 822. Syntheses Involving Preformed Amino-methylene Groups 823. Syntheses Involving an Aminomethylene Group Formed In Situ 904. Syntheses from Malondiamides and Malondiamidine 975. Other Syntheses of Pyrimidines 1016. Formation of Pyrimidine Rmg in Fused Heterocycles 107Chapter IV. Pyrimidine and Its C-Alkyl and C-Aryl Derivatives 1161. Pyrimidine (Unsubstituted) 1162. C-Alkyl- and C-Aryl-pyrimidines 119Chapter V. Nitro-, Nitroso-, and AryIazo-pyrimidines 1381. The Nitropyrimidines 1382. Nitrosopyrimidines 1463. The Arylazopyrimidines 152Chapter VI. Halogenopyrimidines 1621. The Preparation of 2 4. and 6-Halogenopyrimidines 1622. The Preparation of 5-Halogenopyrimidines 1683. The Preparation of Extranuclear Halogenopyrimidines 1764. Properties of Halogenopyrimidines 1815. Reactions of 2-, 4-, and 6-Halogenopyrimidines 1836. Reactions of 5-Halogenopyrimidines 2107. Reactions of Extranuclear Halogenopyrimidines 214Chapter VII. Hydroxy- and Alkoxy-pyrimidines 2271. Preparation of 2 4 and 6-Hydroxypyrimidines 2272. Preparation of 5-Hydroxypyrimidines 2373. Preparation of Extranuclear Hydroxypyrimidines 2414. Preparation of Alkoxy- and Aryloxy-pyrimidines 2455. Properties and Structure of Hydroxy- and Alkoxy-pyrimidines 2496. Reactions of Hydroxypyrimidines 2507. Reactions of AIkoxy- and Aryloxy-pyrimidines 2548. Some Naturally Occurring Hydroxypyrimidines 2569. The Alloxan Group of Pyrimidines 260Chapter VIII. Sulphur-containing Pyrimidines 272I. The Mercaptopyrimidines 2722. The Thioethers: Alkylthio- and Arylthio-pyrimidines 2863. DipyrimidinyI Disulphides and Sulphides 2914. Pyrimidine Sulphonic Acids and Related Compounds 2955. Alkylsulphonylpyrimidines 2986. Thiouracil and Homologues 300Chapter IX. The Aminopyrimidines 3061. Preparation of 2-, 4-, and 6-Aminopyrimidines 3062. Reparation of 5-Aminopyrimidines  3133. Preparation of Extranuclear Aminopyrimidines 3164. Properties of Aminopyrimidines 3205. Reactions of Aminopyrimidines 3216. Urethanes (Alkoxycarbonylaminopyrimidines) 3367. Ureidopyrimidines 3398. Other Substituted-amino-pyrimidines 3419. Some Naturally Occurring Aminopyrimidines 345Chapter X. The N Alylated Pyrimidines and Pyrimidine-N-Oxides 3561. The Oxopyrimidines 3572. The Iminopyrimidines 3773. The N-Methylated Thiopyrirnidines 3814. The Pyrimidine-N-Oxides 382Chapter XI. The Pyrimidine Carboxylic Acids and Related Derivatives 3891. The Carboxypyrimidines 3892. Alkoxycarbonylpyrimidines (Pyrimidine Esters) 3953. Carbamoyipyrimidines (Amidesj and Related Compounds (Hydrazidesand Azides) 3974. Pyrimidine Nitriles 4015. Pyrimidine Aldehydes and Their Acetals 4066. Pyrimidine Ketones and Derivatives 4157. The Isocyanato-. Thiocyanato-. and Isothiocyanato-pyrimidine Family 4188. Orotic Acid: Biosynthesis of Pyrimidines 422Chapter XII. The Reduced Pyrimidines 4301. Preparation of Dihydropyrimidines 4312. Preparation of Tetrahydropyrimidines 4453. Preparation of Hexahydropyrimidines 4524. Reactions of Reduced Pyrimidines 454Chapter XIII The Ionization and Absorption Spectra of Pyrimidines 4641. Ionization of Pyrimidines 4642. The Absorption Spectra of the Pyrimidines (By S. F.Mason) 474