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<p><b>Chapter I. Introduction to the Pyrimidines 1</b></p> <p>1. History 1</p> <p>2. Nomenclature 3</p> <p>3. The Unique Basis of Pyrimidine Chemistry 5</p> <p>4. General Summary of Pyrimidine Chemistry 9</p> <p>5. Physical Properties of Pyrimidines 26</p> <p><b>Chapter II. The Principal Synthetic Method 31</b></p> <p>1. General Scope 31</p> <p>2. Use of β –Dialdehydes 32</p> <p>3. Use of β-Aldehydo Ketones 34</p> <p>4. Use of β Diketones 36</p> <p>5. Use of β-Aldehydo Esters 38</p> <p>6. Use of β-Keto Esters 48</p> <p>7. Use of β-Diesters (Malonic Esters) 51</p> <p>8. Use of β-Aldehydo Nitriles 59</p> <p>9. Use of β -Keto Nitriles 65</p> <p>10. Use of β -Ester Nitriles</p> <p>11. Use of β -Dinitriles (Malononitriles)</p> <p><b>Chapter III. Other Methods of Primary Synthesis 82</b></p> <p>1. General Remarks 82</p> <p>2. Syntheses Involving Preformed Amino-methylene Groups 82</p> <p>3. Syntheses Involving an Aminomethylene Group Formed <i>In Situ</i> 90</p> <p>4. Syntheses from Malondiamides and Malondiamidine 97</p> <p>5. Other Syntheses of Pyrimidines 101</p> <p>6. Formation of Pyrimidine Rmg in Fused Heterocycles 107</p> <p><b>Chapter IV. Pyrimidine and Its C-Alkyl and C-Aryl Derivatives 116</b></p> <p>1. Pyrimidine (Unsubstituted) 116</p> <p>2. C-Alkyl- and C-Aryl-pyrimidines 119</p> <p><b>Chapter V. Nitro-, Nitroso-, and AryIazo-pyrimidines 138</b></p> <p>1. The Nitropyrimidines 138</p> <p>2. Nitrosopyrimidines 146</p> <p>3. The Arylazopyrimidines 152</p> <p><b>Chapter VI. Halogenopyrimidines 162</b></p> <p>1. The Preparation of 2 4. and 6-Halogenopyrimidines 162</p> <p>2. The Preparation of 5-Halogenopyrimidines 168</p> <p>3. The Preparation of Extranuclear Halogenopyrimidines 176</p> <p>4. Properties of Halogenopyrimidines 181</p> <p>5. Reactions of 2-, 4-, and 6-Halogenopyrimidines 183</p> <p>6. Reactions of 5-Halogenopyrimidines 210</p> <p>7. Reactions of Extranuclear Halogenopyrimidines 214</p> <p><b>Chapter VII. Hydroxy- and Alkoxy-pyrimidines 227</b></p> <p>1. Preparation of 2 4 and 6-Hydroxypyrimidines 227</p> <p>2. Preparation of 5-Hydroxypyrimidines 237</p> <p>3. Preparation of Extranuclear Hydroxypyrimidines 241</p> <p>4. Preparation of Alkoxy- and Aryloxy-pyrimidines 245</p> <p>5. Properties and Structure of Hydroxy- and Alkoxy-pyrimidines 249</p> <p>6. Reactions of Hydroxypyrimidines 250</p> <p>7. Reactions of AIkoxy- and Aryloxy-pyrimidines 254</p> <p>8. Some Naturally Occurring Hydroxypyrimidines 256</p> <p>9. The Alloxan Group of Pyrimidines 260</p> <p><b>Chapter VIII. Sulphur-containing Pyrimidines 272</b></p> <p>I. The Mercaptopyrimidines 272</p> <p>2. The Thioethers: Alkylthio- and Arylthio-pyrimidines 286</p> <p>3. DipyrimidinyI Disulphides and Sulphides 291</p> <p>4. Pyrimidine Sulphonic Acids and Related Compounds 295</p> <p>5. Alkylsulphonylpyrimidines 298</p> <p>6. Thiouracil and Homologues 300</p> <p><b>Chapter IX. The Aminopyrimidines 306</b></p> <p>1. Preparation of 2-, 4-, and 6-Aminopyrimidines 306</p> <p>2. Reparation of 5-Aminopyrimidines  313</p> <p>3. Preparation of Extranuclear Aminopyrimidines 316</p> <p>4. Properties of Aminopyrimidines 320</p> <p>5. Reactions of Aminopyrimidines 321</p> <p>6. Urethanes (Alkoxycarbonylaminopyrimidines) 336</p> <p>7. Ureidopyrimidines 339</p> <p>8. Other Substituted-amino-pyrimidines 341</p> <p>9. Some Naturally Occurring Aminopyrimidines 345</p> <p><b>Chapter X. The <i>N</i> Alylated Pyrimidines and Pyrimidine-N-Oxides 356</b></p> <p>1. The Oxopyrimidines 357</p> <p>2. The Iminopyrimidines 377</p> <p>3. The N-Methylated Thiopyrirnidines 381</p> <p>4. The Pyrimidine-N-Oxides 382</p> <p><b>Chapter XI. The Pyrimidine Carboxylic Acids and Related Derivatives 389</b></p> <p>1. The Carboxypyrimidines 389</p> <p>2. Alkoxycarbonylpyrimidines (Pyrimidine Esters) 395</p> <p>3. Carbamoyipyrimidines (Amidesj and Related Compounds (Hydrazidesand Azides) 397</p> <p>4. Pyrimidine Nitriles 401</p> <p>5. Pyrimidine Aldehydes and Their Acetals 406</p> <p>6. Pyrimidine Ketones and Derivatives 415</p> <p>7. The Isocyanato-. Thiocyanato-. and Isothiocyanato-pyrimidine Family 418</p> <p>8. Orotic Acid: Biosynthesis of Pyrimidines 422</p> <p><b>Chapter XII. The Reduced Pyrimidines 430</b></p> <p>1. Preparation of Dihydropyrimidines 431</p> <p>2. Preparation of Tetrahydropyrimidines 445</p> <p>3. Preparation of Hexahydropyrimidines 452</p> <p>4. Reactions of Reduced Pyrimidines 454</p> <p><b>Chapter XIII </b>T<b>he Ionization and Absorption Spectra of Pyrimidines 464</b></p> <p>1. Ionization of Pyrimidines 464</p> <p>2. The Absorption Spectra of the Pyrimidines (By S. F.Mason) 474</p>

<p><b>Desmond J. Brown</b> is Professor of Chemistry at The Australian National University's Research School of Chemistry.</p>

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