The pyrimidines

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The pyrimidines

D.J. Brown ; with an essay by S.F. Mason

(The chemistry of heterocyclic compounds : a series of monographs, v. 16)

Wiley, 1962-85

  • [Original v.]
  • Supplement 1
  • Supplement 2

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Note

"An Interscience publication."

Supplement 2 / with a chapter by R.F. Evans ; and essays by W.B. Cowden and M.D. Fenn

Description and Table of Contents

Volume

[Original v.] ISBN 9780470381151

Description

The Chemistry of Heterocyclic Compounds, since its inception, has been recognized as a cornerstone of heterocyclic chemistry. Each volume attempts to discuss all aspects - properties, synthesis, reactions, physiological and industrial significance - of a specific ring system. To keep the series up-to-date, supplementary volumes covering the recent literature on each individual ring system have been published. Many ring systems (such as pyridines and oxazoles) are treated in distinct books, each consisting of separate volumes or parts dealing with different individual topics. With all authors are recognized authorities, the Chemistry of Heterocyclic Chemistry is considered worldwide as the indispensable resource for organic, bioorganic, and medicinal chemists.

Table of Contents

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

Supplement 2 ISBN 9780471381167

Description

Drawing from over 2,500 papers, this volume eliminates the need for time-consuming literature surveys for pyrimidines from 1970 through 1983. Chapters summarize the major advances in pyrimidine chemistry, detail advances in methods of primary synthesis of pyrimidines, update all aspects of hydropyrimidines, and treat recent advances in the ionization and spectra of pyrimidines.

Table of Contents

  • Introduction to the Pyrimidines (H l, E l). The Principal Synthetic Method (H 3l, E 20). Other Methods of Primary Synthesis (H 82, E 53). Pyrimidine and Its C-Alkyl Derivatives (H ll6, E 86). Nitro-, Nitroso-, and Arylazopyrimidines (H l38, E 94). Halogenopyrimidines (H l62, E ll0). Hydroxyand Alkoxypyrimidines (H 227, E l66). Sulfur-Containing Pyrimidines (H 272, E 202). The Aminopyrimidines (H 306, E 230). The Pyrimidine Carboxylic Acids and Related Derivatives (H 389,E 296). The Reduced Pyrimidines (H 430, E 322
  • by R. F. Evans). Appendix: List of Simple Pyrimidines (H 50l, H Tl). References. Author Index. Subject Index.

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Details

  • NCID
    BA02525712
  • ISBN
    • 0470381159
    • 0471381160
    • 0471381160
  • LCCN
    61009039
  • Country Code
    us
  • Title Language Code
    eng
  • Text Language Code
    eng
  • Place of Publication
    New York ; London
  • Pages/Volumes
    3 v.
  • Size
    24 cm
  • Classification
  • Parent Bibliography ID
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