Mehr lesen
Informationen zum Autor 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. Klappentext 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. Zusammenfassung 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. Inhaltsverzeichnis 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 Synt...
Inhaltsverzeichnis
CHAPTER 1 PRIMARY SYNTHESES OF 1,5-NAPHTHYRIDINES.
1.1 From a Single Aliphatic Substrate.
1.2 From a Single Pyridine Substrate.
1.3 From a Pyridine Substrate with One Synthon.
1.4 From a Pyridine Substrate and Two Synthons.
1.5 From Other Heterocyclic Substrates.
CHAPTER 2 1,5-NAPHTHYRIDINE, ALKYL-1,5- NAPHTHYRIDINES, AND ARYL-1,5- NAPHTHYRIDINES.
2.1 1,5-Naphthyridine.
2.2 Alkyl- and Aryl-1,5-Naphthyridines.
CHAPTER 3 HALOGENO-1,5-NAPHTHYRIDINES.
3.1 Preparation of Halogeno-1,5-Naphthyridines.
3.2 Reactions of Halogeno-1,5-Naphthyridines.
CHAPTER 4 OXY-1,5-NAPHTHYRIDINES.
4.1 Tautomeric 1,5-Naphthyridinones and Extranuclear Hydroxy-1,5-Naphthyridines.
4.2 Alkoxy- and Aryloxy-1,5-Naphthyridines.
4.3 Nontautomeric 1,5-Naphthyridinones.
4.4 1,5-Naphthyridine N-Oxides.
CHAPTER 5 THIO-1,5-NAPHTHYRIDINES.
CHAPTER 6 NITRO-, AMINO-, AND RELATED 1,5-NAPHTHYRIDINES.
6.1 Nitro-1,5-Naphthyridines.
6.2 Amino- and (Substituted-Amino)-1,5-Naphthyridines.
CHAPTER 7 1,5-NAPHTHYRIDINECARBOXYLIC ACIDS AND RELATED DERIVATIVES.
7.1 1,5-Naphthyridinecarboxylic Acids.
7.2 1,5-Naphthyridinecarboxylic Esters.
7.3 1,5-Naphthyridinecarboxamides, Carbonitriles, Carbaldehydes, and Ketones.
CHAPTER 8 PRIMARY SYNTHESES OF 1,6-NAPHTHYRIDINES.
8.1 By Condensation of Two or More Aliphatic Substrates/Synthons.
8.2 From a Single Pyridine Substrate.
8.3 From a Pyridine Substrate with One Synthon.
8.4 From a Pyridine Substrate with Two or More Synthons.
8.5 From Other Heterocyclic Systems.
CHAPTER 9 1,6-NAPHTHYRIDINE, ALKYL-1,6- NAPHTHYRIDINES, AND ARYL-1,6- NAPHTHYRIDINES.
9.1 1,6-Naphthyridine.
9.2 Alkyl- and Aryl-1,6-Naphthyridines.
CHAPTER 10 HALOGENO-1,6-NAPHTHYRIDINES.
10.1 Preparation of Halogeno-1,6-Naphthyridines.
10.2 Reactions of Halogeno-1,6-Naphthyridines.
CHAPTER 11 OXY-1,6-NAPHTHYRIDINES.
11.1 Tautomeric/Nontautomeric 1,6-Naphthyridinones and Extranuclear Hydroxy-1,6-Naphthyridines.
11.2 Alkoxy- and Acyloxy-1,6-Naphthyridines.
11.3 1,6-Naphthyridine N-Oxides.
CHAPTER 12 THIO-1,6-NAPHTHYRIDINES.
CHAPTER 13 NITRO-, AMINO-, AND RELATED 1,6-NAPHTHYRIDINES.
13.1 Nitro-1,6-Naphthyridines.
13.2 Amino- and (Substituted-Amino)-1,6-Naphthyridines.
CHAPTER 14 1,6-NAPHTHYRIDINECARBOXYLIC ACIDS AND RELATED DERIVATIVES.
14.1 1,6-Naphthyridinecarboxylic Acids.
14.2 1,6-Naphthyridinecarboxylic Esters.
14.3 1,6-Naphthyridinecarboxamides.
14.4 1,6-Naphthyridinecarbonitriles, Carbaldehydes, and Ketones.
CHAPTER 15 PRIMARY SYNTHESES OF 1,7-NAPHTHYRIDINES.
15.1 From a Single Aliphatic Substrate.
15.2 From a Single Pyridine Substrate.
15.3 From a Pyridine Substrate with a Synthon.
15.4 From Other Heterocyclic Systems.
CHAPTER 16 1,7-NAPHTHYRIDINE, ALKYL-1,7- NAPHTHYRIDINES, AND ARYL-1,7- NAPHTHYRIDINES.
16.1 1,7-Naphthyridine.
16.2 Alkyl- and Aryl-1,7-Naphthyridines.
CHAPTER 17 HALOGENO-1,7-NAPHTHYRIDINES.
17.1 Preparation of Halogeno-1,7-Naphthyridines.
17.2 Reactions of Halogeno-1,7-Naphthyridines.
CHAPTER 18 OXY-1,7-NAPHTHYRIDINES.
18.1 1,7-Naphthyridinones.
18.2 Alkoxy- and Acyloxy-1,7-Naphthyridines.
18.3 1,7-Naphthyridine N-Oxides.
CHAPTER 19 THIO-1,7-NAPHTHYRIDINES.
CHAPTER 20 NITRO-, AMINO-, AND RELATED 1,7-NAPHTHYRIDINES.
20.1 Nitro-1,7-Naphthyridines.
20.2 Amino-1,7-Naphthyridines.
CHAPTER 21 1,7-NAPHTHYRIDINECARBOXYLIC ACIDS AND RELATED DERIVATIVES.
21.1 1,7-Naphthyridinecarboxylic Acids.
21.2 1,7-Naphthyridinecarboxylic Esters.
21.3 1,7-Naphthyridinecarboxamides.
21.4 1,7-Naphthyridinecarbonitriles.
21.5 1,7-Naphthyridinecarbaldehydes and Ketones.
CHAPTER 22 PRIMARY SYNTHESES OF 1,8-NAPHTHYRIDINES.
22.1 From an Aliphatic Substrate.
22.2 From a Single Pyridine Substrate.
22.3 From a Pyridine Substrate and Synthon(s).
22.4 From Other Heterocyclic Substrates.
CHAPTER 23 1,8-NAPHTHYRIDINE, ALKYL-1,8- NAPHTHYRIDINES, AND ARYL-1,8
