Desmond J. Brown, Jonathan A. Ellman, Edward C. Taylor

The Naphthyridines, Volume 63 (eBook, PDF)

• Format: PDF

Produktbeschreibung

A volume in the Chemistry of Heterocyclic Compounds series, this book provides a summary of the chemistry of each of the six naphthyridine systems along with tables of known simple derivatives with original references. Each of the six naphthyridine systems are described in valuable detail and coverage includes: Primary synthetic methods from non-naphthyridine substrates; Chemistry and properties of the parent heterocycle and its simple alkyl derivatives; Formation and reactions of halogeno derivatives; formation and reactions of hydroxy, oxo, alkoxy, and related derivatives.

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Produktdetails

• Verlag: John Wiley & Sons
• Seitenzahl: 448
• Erscheinungstermin: 28. Juni 2008
• Englisch
• ISBN-13: 9780470181157
• Artikelnr.: 37291140

Autorenporträt

Author Desmond J. Brown is Professor of Chemistry at The Australian National University's Research School of Chemistry. Series Editor Edward C. Taylor is a Professor in the Department of Chemisry at Princeton University.

Inhaltsangabe

Chapter 1 Primary Syntheses of 1,5
Naphthyridines 1 1.1 From a Single Aliphatic Substrate 1 1.2 From a Single Pyridine Substrate 2 1.2.1 By Formation of the N1,C2
Bond 2 1.2.2 By Formation of the C3,C4
Bond 3 1.2.3 By Formation of the C4,C4a
Bond 4 1.3 From a Pyridine Substrate with One Synthon 5 1.3.1 Where the Synthon Supplies One Atom 5 1.3.2 Where the Synthon Supplies Two Atoms 6 1.3.3 Where the Synthon Supplies Three Atoms 7 1.4 From a Pyridine Substrate and Two Synthons 9 1.5 From Other Heterocyclic Substrates 10 Chapter 2 1,5
Naphthyridine, Alkyl
1,5
Naphthyridines, and Aryl
1,5
Naphthyridines 13 2.1 1,5
Naphthyridine 13 2.1.1 Preparation of 1,5
Naphthyridine 13 2.1.2 Properties of 1,5
Naphthyridine 14 2.1.3 Reactions of 1,5
Naphthyridine 16 2.2 Alkyl
and Aryl
1,5
Naphthyridines 19 2.2.1 Preparation of Alkyl
and Aryl
1,5
Naphthyridines 20 2.2.2 Reactions of Alkyl
and Aryl
1,5
Naphthyridines 22 Chapter 3 Halogeno
1,5
Naphthyridines 25 3.1 Preparation of Halogeno
1,5
Naphthyridines 25 3.1.1 By Direct Halogenation 25 3.1.2 By Halogenolysis of 1,5
Naphthyridinones or the Like 26 3.1.3 By the Meissenheimer Reaction on 1,5
Naphthyridine N
Oxides 29 3.1.4 By Miscellaneous Procedures 31 3.2 Reactions of Halogeno
1,5
Naphthyridines 31 3.2.1 Alcoholysis or Phenolysis of Halogeno
1, 5
Naphthyridines 31 3.2.2 Aminolysis of Halogeno
1,5
Naphthyridines 34 3.2.3 Other Reactions of Halogeno
1,5
Naphthyridines 38 Chapter 4 Oxy
1,5
Naphthyridines 43 4.1 Tautomeric 1,5
Naphthyridinones and Extranuclear Hydroxy
1,5
Naphthyridines 43 4.1.1 Preparation of Tautomeric 1,5
Naphthyridinones and the Like 44 4.1.2 Reactions of Tautomeric 1,5
Naphthyridinones and the Like 46 4.2 Alkoxy
and Aryloxy
1,5
Naphthyridines 48 4.3 Nontautomeric 1,5
Naphthyridinones 49 4.4 1,5
Naphthyridine N
Oxides 50 Chapter 5 Thio
1,5
Naphthyridines 53 Chapter 6 Nitro
, Amino
, and Related 1,5
Naphthyridines 55 6.1 Nitro
1,5
Naphthyridines 55 6.1.1 Preparation of Nitro
1,5
Naphthyridines 55 6.1.2 Reactions of Nitro
1,5
Naphthyridines 56 6.2 Amino
and (Substituted
Amino)
1,5
Naphthyridines 57 6.2.1 Preparation of Amino
1,5
Naphthyridines 58 6.2.2 Reactions of Amino
1,5
Naphthyridines 58 Chapter 7 1,5
Naphthyridinecarboxylic Acids and Related Derivatives 61 7.1 1,5
Naphthyridinecarboxylic Acids 61 7.2 1,5
Naphthyridinecarboxylic Esters 64 7.3 1,5
Naphthyridinecarboxamides, Carbonitriles, Carbaldehydes, and Ketones 65 Chapter 8 Primary Syntheses of 1,6
Naphthyridines 67 8.1 By Condensation of Two or More Aliphatic Substrates/Synthons 67 8.2 From a Single Pyridine Substrate 69 8.3 From a Pyridine Substrate with One Synthon 75 8.3.1 Where the Synthon Supplies One Ring Atom 76 8.3.2 Where the Synthon Supplies Two Ring Atoms 78 8.3.3 Where the Synthon Supplies Three or More Ring Atoms 81 8.4 From a Pyridine Substrate with Two or More Synthons 83 8.5 From Other Heterocyclic Systems 84 Chapter 9 1,6
Naphthyridine, Alkyl
1,6
Naphthyridines, and Aryl
1,6
Naphthyridines 91 9.1 1,6
Naphthyridine 91 9.1.1 Preparation of 1,6
Naphthyridine 91 9.1.2 Properties of 1,6
Naphthyridine 93 9.1.3 Reactions of 1,6
Naphthyridines 94 9.2 Alkyl
and Aryl
1,6
Naphthyridines 97 9.2.1 Preparation of Alkyl
and Aryl
1,6
Naphthyridines 97 9.2.2 Reactions of Alkyl
and Aryl
1,6
Naphthyridines 99 Chapter 10 Halogeno
1,6
Naphthyridines 103 10.1 Preparation of Halogeno
1,6
Naphthyridines 103 10.1.1 By Direct Halogenation 103 10.1.2 By Halogenolysis of 1,6
Naphthyridinones or the Like 104 10.1.3 By Other Methods 107 10.2 Reactions of Halogeno
1,6
Naphthyridines 108 10.2.1 Alcoholysis or Phenolysis of Halogeno
1, 6
Naphthyridines 108 10.2.2 Aminolysis of Halogeno
1,6
Naphthyridines 110 10.2.3 Dehalogenation of Halogeno
1,6
Naphthyridines 111 10.2.4 Other Reactions of Halogeno
1,6
Naphthyridines 113 Chapter 11 Oxy
1,6
Naphthyridines 115 11.1 Tautomeric/Nontautomeric 1,6
Naphthyridinones and Extranuclear Hydroxy
1,6
Naphthyridines 115 11.1.1 Preparation of 1,6
Naphthyridinones and the Like 116 11.1.2 Reactions of 1,6
Naphthyridinones and the Like 118 11.2 Alkoxy
and Acyloxy
1,6
Naphthyridines 120 11.3 1,6
Naphthyridine N
Oxides 121 Chapter 12 Thio
1,6
Naphthyridines 125 Chapter 13 Nitro
, Amino
, and Related 1,6
Naphthyridines 127 13.1 Nitro
1,6
Naphthyridines 127 13.1.1 Preparation of Nitro
1,6
Naphthyridines 127 13.1.2 Reactions of Nitro
1,6
Naphthyridines 128 13.2 Amino
and (Substituted
Amino)
1,6
Naphthyridines 129 13.2.1 Preparation of Amino
1,6
Naphthyridines 130 13.2.2 Reactions of Amino
1,6
Naphthyridines 131 Chapter 14 1,6
Naphthyridinecarboxylic Acids and Related Derivatives 135 14.1 1,6
Naphthyridinecarboxylic Acids 135 14.1.1 Preparation of 1,6
Naphthyridinecarboxylic Acids 135 14.1.2 Reactions of 1,6
Naphthyridinecarboxylic Acids 137 14.2 1,6
Naphthyridinecarboxylic Esters 139 14.3 1,6
Naphthyridinecarboxamides 139 14.4 1,6
Naphthyridinecarbonitriles, Carbaldehydes, and Ketones 141 Chapter 15 Primary Syntheses of 1,7
Naphthyridines 143 15.1 From a Single Aliphatic Substrate 143 15.2 From a Single Pyridine Substrate 143 15.3 From a Pyridine Substrate with a Synthon 147 15.4 From Other Heterocyclic Systems 150 Chapter 16 1,7
Naphthyridine, Alkyl
1,7
Naphthyridines, and Aryl
1,7
Naphthyridines 153 16.1 1,7
Naphthyridine 153 16.1.1 Preparation of 1,7
Naphthyridine 153 16.1.2 Properties of 1,7
Naphthyridine 154 16.1.3 Reactions of 1,7
Naphthyridine 155 16.2 Alkyl
and Aryl
1,7
Naphthyridines 157 16.2.1 Preparation of Alkyl
and Aryl
1,7
Naphthyridines 157 16.2.2 Reactions of Alkyl
and Aryl
1,7
Naphthyridines 158 Chapter 17 Halogeno
1,7
Naphthyridines 161 17.1 Preparation of Halogeno
1,7
Naphthyridines 161 17.2 Reactions of Halogeno
1,7
Naphthyridines 163 Chapter 18 Oxy
1,7
Naphthyridines 167 18.1 1,7
Naphthyridinones 167 18.1.1 Preparation of 1,7
Naphthyridinones 167 18.1.2 Reactions of 1,7
Naphthyridinones 168 18.2 Alkoxy
and Acyloxy
1,7
Naphthyridines 170 18.3 1,7
Naphthyridine N
Oxides 171 Chapter 19 Thio
1,7
Naphthyridines 173 Chapter 20 Nitro
, Amino
, and Related 1,7
Naphthyridines 175 20.1 Nitro
1,7
Naphthyridines 175 20.2 Amino
1,7
Naphthyridines 176 Chapter 21 1,7
Naphthyridinecarboxylic Acids and Related Derivatives 179 21.1 1,7
Naphthyridinecarboxylic Acids 179 21.1.1 Preparation of 1,7
Naphthyridinecarboxylic Acids 179 21.1.2 Reactions of 1,7
Naphthyridinecarboxylic Acids 180 21.2 1,7
Naphthyridinecarboxylic Esters 182 21.3 1,7
Naphthyridinecarboxamides 182 21.4 1,7
Naphthyridinecarbonitriles 182 21.5 1,7
Naphthyridinecarbaldehydes and Ketones 182 Chapter 22 Primary Syntheses of 1,8
Naphthyridines 183 22.1 From an Aliphatic Substrate 183 22.2 From a Single Pyridine Substrate 184 22.3 From a Pyridine Substrate and Synthon(s) 187 22.4 From Other Heterocyclic Substrates 192 Chapter 23 1,8
Naphthyridine, Alkyl
1,8
Naphthyridines, and Aryl
1,8
Naphthyridines 197 23.1 1,8
Naphthyridine and Hydro Derivatives 197 23.1.1 Preparation of 1,8
Naphthyridine 197 23.1.2 Properties of 1,8
Naphthyridine 198 23.1.3 1,8
Naphthyridine Complexes 199 23.1.4 Reactions of 1,8
Naphthyridine 200 23.2 Alkyl
and Aryl
1,8
Naphthyridines 203 23.2.1 Preparation of Alkyl
and Aryl
1,8
Naphthyridines 203 23.2.2 Reactions of Alkyl
and Aryl
1,8
Naphthyridines 205 Chapter 24 Halogeno
1,8
Naphthyridines 209 24.1 Preparation of Halogeno
1,8
Naphthyridines 209 24.2 Reactions of Halogeno
1,8
Naphthyridines 214 Chapter 25 Oxy
1,8
Naphthyridines 221 25.1 1,8
Naphthyridinones and the Like 221 25.1.1 Preparation of 1,8
Naphthyridinones and the Like 221 25.1.2 Reactions of 1,8
Naphthyridinones and the Like 224 25.2 Alkoxy
and Aryloxy
1,8
Naphthyridines 227 25.3 1,8
Naphthyridine N
Oxides 228 Chapter 26 Thio
1,8
Naphthyridines 231 26.1 1,8
Naphthyridinethiones 231 26.2 Alkylthio
and Arylthio
1,8
Naphthyridines 232 26.3 1,8
Naphthyridine Sulfoxides and Sulfones 232 26.4 1,8
Naphthyridinesulfonic Acids and the Like 233 Chapter 27 Nitro
, Amino
, and Related 1,8
Naphthyridines 235 27.1 Nitro
1,8
Naphthyridines 235 27.1.1 Preparation of Nitro
1,8
Naphthyridines 235 27.1.2 Reactions of Nitro
1,8
Naphthyridines 237 27.2 Nitroso
1,8
Naphthyridines 238 27.3 Amino
1,8
Naphthyridines 238 27.3.1 Preparation of Amino
1,8
Naphthyridines 238 27.3.2 Reactions of Amino
1,8
Naphthyridines 241 Chapter 28 1,8
Naphthyridinecarboxylic Acids and Related Derivatives 247 28.1 1,8
Naphthyridinecarboxylic Acids 247 28.1.1 Preparation of 1,8
Naphthyridinecarboxylic Acids 247 28.1.2 Reactions of 1,8
Naphthyridinecarboxylic Acids 249 28.2 1,8
Naphthyridinecarbonyl Halides 251 28.3 1,8
Naphthyridinecarboxylic Esters 252 28.3.1 Preparation of 1,8
Naphthyridinecarboxylic Esters 252 28.3.2 Reactions of 1,8
Naphthyridinecarboxylic Esters 252 28.4 1,8
Naphthyridinecarboxamides 254 28.4.1 Preparation of 1,8
Naphthyridinecarboxamides 254 28.4.2 Reactions of 1,8
Naphthyridinecarboxamides 255 28.5 1,8
Naphthyridinecarbonitriles 257 28.6 1,8
Naphthyridinecarbaldehydes and Related Ketones 257 28.6.1 Preparation of the Carbaldehydes and Ketones 257 28.6.2 Reactions of the Carbaldehydes and Ketones 259 Chapter 29 The 2,6
Naphthyridines 261 29.1 Primary Syntheses of 2,6
Naphthyridines 261 29.1.1 2,6
Naphthyridines by Cyclization of Pyridine Derivatives 261 29.1.2 2,6
Naphthyridines by Cyclocondensation of a Pyridine Derivative with a Synthon 263 29.1.3 2,6
Naphthyridines from Other Heterocyclic Substrates 264 29.2 2,6
Naphthyridine and Alkyl
2,6
Naphthyridines 265 29.2.1 Preparation of 2,6
Naphthyridine 266 29.2.2 Properties of 2,6
Naphthyridine 266 29.3 Halogeno
2,6
Naphthyridines 267 29.3.1 Preparation of Halogeno
2,6
Naphthyridines 267 29.3.2 Reactions of Halogeno
2,6
Naphthyridines 268 29.4 Oxy
2,6
Naphthyridines 269 29.5 Thio
2,6
Naphthyridines 270 29.6 Nitro
, Amino
, and Related 2,6
Naphthyridines 271 29.6.1 Preparation of Amino
2,6
Naphthyridines 271 29.6.2 Reactions of Amino
2,6
Naphthyridines 272 29.7 2,6
Naphthyridinecarboxylic Acids and Related Derivatives 272 Chapter 30 The 2,7
Naphthyridines 275 30.1 Primary Syntheses of 2,7
Naphthyridines 275 30.1.1 2,7
Naphthyridines from Nonheterocyclic Precursors 275 30.1.2 2,7
Naphthyridines by Cyclization of Pyridine Substrates 277 30.1.3 2,7
Naphthyridines by Cyclocondensation of Pyridine Substrates with Synthons 278 30.1.4 2,7
Naphthyridines from Other Heterocyclic Substrates 280 30.2 2,7
Naphthyridine and Alkyl
2,7
Naphthyridines 283 30.2.1 Preparation of 2,7
Naphthyridine 283 30.2.2 Properties of 2,7
Naphthyridine 283 30.2.3 Reactions of 2,7
Naphthyridine 284 30.3 Halogeno
2,7
Naphthyridines 285 30.3.1 Preparation of Halogeno
2,7
Naphthyridines 286 30.3.2 Reactions of Halogeno
2,7
Naphthyridines 287 30.4 Oxy
2,7
Naphthyridines 289 30.5 Thio
2,7
Naphthyridines 290 30.6 Nitro
, Amino
, and Related 2,7
Naphthyridines 290 30.7 2,7
Naphthyridinecarboxylic Acids and Related Derivatives 291 30.7.1 2,7
Naphthyridinecarboxylic Acids 291 30.7.2 2,7
Naphthyridinecarboxylic Esters 292 30.7.3 2,7
Naphthyridinecarboxamides and Carbonitriles 293 30.7.4 2,7
Naphthyridinecarbaldehydes and Ketones 293 References 295 Appendix Tables of Simple Naphthyridines 337 Table A.1 Alphabetical List of Simple 1,5
Naphthyridines 339 Table A.2 Alphabetical List of Simple 1,6
Naphthyridines 348 Table A.3 Alphabetical List of Simple 1,7
Naphthyridines 361 Table A.4 Alphabetical List of Simple 1,8
Naphthyridines 366 Table A.5 Alphabetical List of Simple 2,6
Naphthyridines 409 Table A.6 Alphabetical List of Simple 2,7
Naphthyridines 411 Index 415