The Chemistry of Heterocyclic Compounds

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.

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–NAPHTHYRIDINES. 23.1 1,8–Naphthyridine and Hydro Derivatives. 23.2 Alkyl– and Aryl–1,8–Naphthyridines. CHAPTER 24 HALOGENO–1,8–NAPHTHYRIDINES. 24.1 Preparation of Halogeno–1,8–Naphthyridines. 24.2 Reactions of Halogeno–1,8–Naphthyridines. CHAPTER 25 OXY–1,8–NAPHTHYRIDINES. 25.1 1,8–Naphthyridinones and the Like. 25.2 Alkoxy– and Aryloxy–1,8–Naphthyridines. 25.3 1,8–Naphthyridine N–Oxides. CHAPTER 26 THIO–1,8–NAPHTHYRIDINES. 26.1 1,8–Naphthyridinethiones. 26.2 Alkylthio– and Arylthio–1,8–Naphthyridines. 26.3 1,8–Naphthyridine Sulfoxides and Sulfones. 26.4 1,8–Naphthyridinesulfonic Acids and the Like. CHAPTER 27 NITRO–, AMINO–, AND RELATED 1,8–NAPHTHYRIDINES. 27.1 Nitro–1,8–Naphthyridines. 27.2 Nitroso–1,8–Naphthyridines. 27.3 Amino–1,8–Naphthyridines. CHAPTER 28 1,8–NAPHTHYRIDINECARBOXYLIC ACIDS AND RELATED DERIVATIVES. 28.1 1,8–Naphthyridinecarboxylic Acids. 28.2 1,8–Naphthyridinecarbonyl Halides. 28.3 1,8–Naphthyridinecarboxylic Esters. 28.4 1,8–Naphthyridinecarboxamides. 28.5 1,8–Naphthyridinecarbonitriles. 28.6 1,8–Naphthyridinecarbaldehydes and Related Ketones. CHAPTER 29 THE 2,6–NAPHTHYRIDINES. 29.1 Primary Syntheses of 2,6–Naphthyridines. 29.2 2,6–Naphthyridine and Alkyl–2,6–Naphthyridines. 29.3 Halogeno–2,6–Naphthyridines. 29.4 Oxy–2,6–Naphthyridines. 29.5 Thio–2,6–Naphthyridines. 29.6 Nitro–, Amino–, and Related 2,6–Naphthyridines. 29.7 2,6–Naphthyridinecarboxylic Acids and Related Derivatives. CHAPTER 30 THE 2,7–NAPHTHYRIDINES. 30.1 Primary Syntheses of 2,7–Naphthyridines. 30.2 2,7–Naphthyridine and Alkyl–2,7–Naphthyridines. 30.3 Halogeno–2,7–Naphthyridines. 30.4 Oxy–2,7–Naphthyridines. 30.5 Thio–2,7–Naphthyridines. 30.6 Nitro–, Amino–, and Related 2,7–Naphthyridines. 30.7 2,7–Naphthyridinecarboxylic Acids and Related Derivatives. REFERENCES. APPENDIX TABLES OF SIMPLE NAPHTHYRIDINES. INDEX.