LEADER 05045nam 2200649Ia 450 001 9910841668503321 005 20230421044607.0 010 $a1-282-24226-1 010 $a9786613813381 010 $a0-470-18739-5 010 $a0-470-18891-X 035 $a(CKB)1000000000376595 035 $a(EBL)469255 035 $a(OCoLC)729013561 035 $a(SSID)ssj0000342011 035 $a(PQKBManifestationID)11277114 035 $a(PQKBTitleCode)TC0000342011 035 $a(PQKBWorkID)10270777 035 $a(PQKB)10193873 035 $a(MiAaPQ)EBC469255 035 $a(EXLCZ)991000000000376595 100 $a19921023d1994 uy 0 101 0 $aeng 135 $aur|n|---||||| 181 $ctxt 182 $cc 183 $acr 200 14$aThe pyrimidines$b[electronic resource] /$fD.J. Brown; with a chapter by R.F. Evans and sections by W.B. Cowden and M.D. Fenn 210 $aNew York $cWiley$dc1994 215 $a1 online resource (1542 p.) 225 1 $aThe Chemistry of heterocyclic compounds ;$vv. 52 300 $a"An Interscience publication." 311 $a0-471-50656-7 320 $aIncludes bibliographical references (p. 1183-1364) and index. 327 $aTHE PYRIMIDINES; Contents; LIST OF TABLES; List of Tables; CHAPTER 1. INTRODUCTION TO PYRIMIDINE CHEMISTRY; 1.1 History and Reviews; 1.2 Nomenclature; 1.3 Factors in the Uniquity of Pyrimidine Chemistry; 1.3.1 The Activated 2- and 4/6-Positions; Table 1.1 Trivial Names of Pyrimidines; 1.3.2 The Semiaromatic 5-Position; 1.3.3 The Effect of Electron-Donating Groups; 1.3.4 The Effect of Electron-Withdrawing Groups; 1.3.5 The Effect of Tautomeric Groups; 1.4 The Primary Synthesis of Pyrimidines; 1.5 Reactions at the Pyrimidine Ring; 1.5.1 Electrophilic Attack; 1.5.1.1 Nitration 327 $a1.5.1.2 Nitrosation1.5.1.3 Diazo Coupling; 1.5.1.4 Halogenation; 1.5.1.5 Sulfonation; 1.5.1.6 C-Formylation; 1.5.1.7 Hydroxy- or Aminomethylation; 1.5.1.8 Formation of Dipyrimidin-5-yl Sulfides; 1.5.2 Nucleophilic Attack; 1.5.2.1 Amination; 1.5.2.2 Hydroxylation; 1.5.2.3 C-Alkylation or Arylation; 1.5.3 Free Radical Attack; 1.5.4 Photochemical Reactions; 1.5.5 Oxidative Reactions; 1.5.6 Nuclear Reduction; 1.5.7 Quaternization at Ring Nitrogen; 1.6 Reactions at Substituents on the Pyrimidine Ring; 1.6.1 Reactions at Alkyl Groups; 1.6.2 Reactions at Aryl Groups 327 $a1.6.3 Reactions at Halogeno Substituents1.6.4 Reactions at Tautomeric Oxo Substituents; 1.6.5 Reactions at Nontautomeric Oxo Substituents; 1.6.6 Reactions at Alkoxy Groups; 1.6.7 Reactions at 5-Hydroxy Groups; 1.6.8 Reactions at N-Oxides; 1.6.9 Reactions at Tautomeric Thioxo Substituents; 1.6.10 Reactions at Nontautomeric Thioxo Substituents; 1.6.11 Reactions at Alkylthio Groups; 1.6.12 Reactions at 5-Mercapto Groups; 1.6.13 Reactions at Sulfo and Related Groups; 1.6.14 Reactions at Alkylsulfonyl and Alkylsulfinyl Groups; 1.6.15 Reactions at Amino Groups 327 $a1.6.16 Reactions at Nitro, Nitroso, and Arylazo Groups1.6.17 Reactions at Carboxy Groups; 1.6.18 Reactions at Alkoxycarbonyl Groups; 1.6.19 Reactions at Carbamoyl Groups; 1.6.20 Reactions at Cyano Groups; 1.6.21 Reactions at C-Formyl Groups; 1.6.22 Reactions at Other C-Acyl Groups; 1.6.23 Reactions at Cyanato and Thiocyanato Groups; 1.6.24 Reactions at Isocyanato and Isothiocyanato Groups; 1.6.25 Reactions at Nitrile Oxide Groups; CHAPTER 2. PRIMARY SYNTHESES; 2.1 From a Single Six-Atom Synthone; 2.1.1 By Completion of the N1-C2 Bond; 2.1.2 By Completion of the N3-C4 Bond 327 $a2.1.3 By Completion of the C4-C5 Bond2.1.4 By Rearrangement of One Pyrimidine into Another; 2.2 From Two Synthones; 2.2.1 By Using a One- and a Five-Atom Synthone; 2.2.1.1 Where the One-Atom Synthone Provides Nl; 2.2.1.2 Where the One-Atom Synthone Provides C2; 2.2.1.3 Where the One-Atom Synthone Provides C4; 2.2.1.4 Where the One-Atom Synthone Provides C5; 2.2.2 By Using a Two- and a Four-Atom Synthone; 2.2.2.1 Where the Two-Atom Synthone Provides Nl + C2; 2.2.2.2 Where the Two-Atom Synthone Provides N3 + C4; 2.2.2.3 Where the Two-Atom Synthone Provides C4 + C5 327 $a2.2.3 By Using Two Three-Atom Synthones 330 $aPrimary Syntheses. The Principal Synthesis. Pyrimidine, Alkylpyrimidines, and Arylpyrimidines. Nitro-, Nitroso-, and Arylazopyrimidines. Halogenopyrimidines. Oxypyrimidines. Thiopyrimidines. Aminopyrimidines. Pyrimidinecarboxylic Acids and Related Derivatives. The Reduced Pyrimidines. The Ionization and Spectra of Pyrimidines. Appendix. References. Subject Index. 410 0$aChemistry of heterocyclic compounds ;$vv. 52. 606 $aPyrimidines 606 $aHeterocyclic compounds 615 0$aPyrimidines. 615 0$aHeterocyclic compounds. 676 $a547.593 676 $a547/.59/05 676 $a547/.593 700 $aBrown$b D. J$0383088 801 0$bMiAaPQ 801 1$bMiAaPQ 801 2$bMiAaPQ 906 $aBOOK 912 $a9910841668503321 996 $aThe pyrimidines$91996097 997 $aUNINA