The Naphthyridines, Volume 63

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.

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/N