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 11.1 From a Single Aliphatic Substrate 11.2 From a Single Pyridine Substrate 21.2.1 By Formation of the N1,C2-Bond 21.2.2 By Formation of the C3,C4-Bond 31.2.3 By Formation of the C4,C4a-Bond 41.3 From a Pyridine Substrate with One Synthon 51.3.1 Where the Synthon Supplies One Atom 51.3.2 Where the Synthon Supplies Two Atoms 61.3.3 Where the Synthon Supplies Three Atoms 71.4 From a Pyridine Substrate and Two Synthons 91.5 From Other Heterocyclic Substrates 10Chapter 2 1,5-Naphthyridine, Alkyl-1,5-Naphthyridines, and Aryl-1,5-Naphthyridines 132.1 1,5-Naphthyridine 132.1.1 Preparation of 1,5-Naphthyridine 132.1.2 Properties of 1,5-Naphthyridine 142.1.3 Reactions of 1,5-Naphthyridine 162.2 Alkyl- and Aryl-1,5-Naphthyridines 192.2.1 Preparation of Alkyl- and Aryl-1,5-Naphthyridines 202.2.2 Reactions of Alkyl- and Aryl-1,5-Naphthyridines 22Chapter 3 Halogeno-1,5-Naphthyridines 253.1 Preparation of Halogeno-1,5-Naphthyridines 253.1.1 By Direct Halogenation 253.1.2 By Halogenolysis of 1,5-Naphthyridinones or the Like 263.1.3 By the Meissenheimer Reaction on 1,5-Naphthyridine N-Oxides 293.1.4 By Miscellaneous Procedures 313.2 Reactions of Halogeno-1,5-Naphthyridines 313.2.1 Alcoholysis or Phenolysis of Halogeno-1, 5-Naphthyridines 313.2.2 Aminolysis of Halogeno-1,5-Naphthyridines 343.2.3 Other Reactions of Halogeno-1,5-Naphthyridines 38Chapter 4 Oxy-1,5-Naphthyridines 434.1 Tautomeric 1,5-Naphthyridinones and Extranuclear Hydroxy-1,5-Naphthyridines 434.1.1 Preparation of Tautomeric 1,5-Naphthyridinones and the Like 444.1.2 Reactions of Tautomeric 1,5-Naphthyridinones and the Like 464.2 Alkoxy- and Aryloxy-1,5-Naphthyridines 484.3 Nontautomeric 1,5-Naphthyridinones 494.4 1,5-Naphthyridine N-Oxides 50Chapter 5 Thio-1,5-Naphthyridines 53Chapter 6 Nitro-, Amino-, and Related 1,5-Naphthyridines 556.1 Nitro-1,5-Naphthyridines 556.1.1 Preparation of Nitro-1,5-Naphthyridines 556.1.2 Reactions of Nitro-1,5-Naphthyridines 566.2 Amino- and (Substituted-Amino)-1,5-Naphthyridines 576.2.1 Preparation of Amino-1,5-Naphthyridines 586.2.2 Reactions of Amino-1,5-Naphthyridines 58Chapter 7 1,5-Naphthyridinecarboxylic Acids and Related Derivatives 617.1 1,5-Naphthyridinecarboxylic Acids 617.2 1,5-Naphthyridinecarboxylic Esters 647.3 1,5-Naphthyridinecarboxamides, Carbonitriles, Carbaldehydes, and Ketones 65Chapter 8 Primary Syntheses of 1,6-Naphthyridines 678.1 By Condensation of Two or More Aliphatic Substrates/Synthons 678.2 From a Single Pyridine Substrate 698.3 From a Pyridine Substrate with One Synthon 758.3.1 Where the Synthon Supplies One Ring Atom 768.3.2 Where the Synthon Supplies Two Ring Atoms 788.3.3 Where the Synthon Supplies Three or More Ring Atoms 818.4 From a Pyridine Substrate with Two or More Synthons 838.5 From Other Heterocyclic Systems 84Chapter 9 1,6-Naphthyridine, Alkyl-1,6-Naphthyridines, and Aryl-1,6-Naphthyridines 919.1 1,6-Naphthyridine 919.1.1 Preparation of 1,6-Naphthyridine 919.1.2 Properties of 1,6-Naphthyridine 939.1.3 Reactions of 1,6-Naphthyridines 949.2 Alkyl- and Aryl-1,6-Naphthyridines 979.2.1 Preparation of Alkyl- and Aryl-1,6-Naphthyridines 979.2.2 Reactions of Alkyl- and Aryl-1,6-Naphthyridines 99Chapter 10 Halogeno-1,6-Naphthyridines 10310.1 Preparation of Halogeno-1,6-Naphthyridines 10310.1.1 By Direct Halogenation 10310.1.2 By Halogenolysis of 1,6-Naphthyridinones or the Like 10410.1.3 By Other Methods 10710.2 Reactions of Halogeno-1,6-Naphthyridines 10810.2.1 Alcoholysis or Phenolysis of Halogeno-1, 6-Naphthyridines 10810.2.2 Aminolysis of Halogeno-1,6-Naphthyridines 11010.2.3 Dehalogenation of Halogeno-1,6-Naphthyridines 11110.2.4 Other Reactions of Halogeno-1,6-Naphthyridines 113Chapter 11 Oxy-1,6-Naphthyridines 11511.1 Tautomeric/Nontautomeric 1,6-Naphthyridinones and Extranuclear Hydroxy-1,6-Naphthyridines 11511.1.1 Preparation of 1,6-Naphthyridinones and the Like 11611.1.2 Reactions of 1,6-Naphthyridinones and the Like 11811.2 Alkoxy- and Acyloxy-1,6-Naphthyridines 12011.3 1,6-Naphthyridine N-Oxides 121Chapter 12 Thio-1,6-Naphthyridines 125Chapter 13 Nitro-, Amino-, and Related 1,6-Naphthyridines 12713.1 Nitro-1,6-Naphthyridines 12713.1.1 Preparation of Nitro-1,6-Naphthyridines 12713.1.2 Reactions of Nitro-1,6-Naphthyridines 12813.2 Amino- and (Substituted-Amino)-1,6-Naphthyridines 12913.2.1 Preparation of Amino-1,6-Naphthyridines 13013.2.2 Reactions of Amino-1,6-Naphthyridines 131Chapter 14 1,6-Naphthyridinecarboxylic Acids and Related Derivatives 13514.1 1,6-Naphthyridinecarboxylic Acids 13514.1.1 Preparation of 1,6-Naphthyridinecarboxylic Acids 13514.1.2 Reactions of 1,6-Naphthyridinecarboxylic Acids 13714.2 1,6-Naphthyridinecarboxylic Esters 13914.3 1,6-Naphthyridinecarboxamides 13914.4 1,6-Naphthyridinecarbonitriles, Carbaldehydes, and Ketones 141Chapter 15 Primary Syntheses of 1,7-Naphthyridines 14315.1 From a Single Aliphatic Substrate 14315.2 From a Single Pyridine Substrate 14315.3 From a Pyridine Substrate with a Synthon 14715.4 From Other Heterocyclic Systems 150Chapter 16 1,7-Naphthyridine, Alkyl-1,7-Naphthyridines, and Aryl-1,7-Naphthyridines 15316.1 1,7-Naphthyridine 15316.1.1 Preparation of 1,7-Naphthyridine 15316.1.2 Properties of 1,7-Naphthyridine 15416.1.3 Reactions of 1,7-Naphthyridine 15516.2 Alkyl- and Aryl-1,7-Naphthyridines 15716.2.1 Preparation of Alkyl- and Aryl-1,7-Naphthyridines 15716.2.2 Reactions of Alkyl- and Aryl-1,7-Naphthyridines 158Chapter 17 Halogeno-1,7-Naphthyridines 16117.1 Preparation of Halogeno-1,7-Naphthyridines 16117.2 Reactions of Halogeno-1,7-Naphthyridines 163Chapter 18 Oxy-1,7-Naphthyridines 16718.1 1,7-Naphthyridinones 16718.1.1 Preparation of 1,7-Naphthyridinones 16718.1.2 Reactions of 1,7-Naphthyridinones 16818.2 Alkoxy- and Acyloxy-1,7-Naphthyridines 17018.3 1,7-Naphthyridine N-Oxides 171Chapter 19 Thio-1,7-Naphthyridines 173Chapter 20 Nitro-, Amino-, and Related 1,7-Naphthyridines 17520.1 Nitro-1,7-Naphthyridines 17520.2 Amino-1,7-Naphthyridines 176Chapter 21 1,7-Naphthyridinecarboxylic Acids and Related Derivatives 17921.1 1,7-Naphthyridinecarboxylic Acids 17921.1.1 Preparation of 1,7-Naphthyridinecarboxylic Acids 17921.1.2 Reactions of 1,7-Naphthyridinecarboxylic Acids 18021.2 1,7-Naphthyridinecarboxylic Esters 18221.3 1,7-Naphthyridinecarboxamides 18221.4 1,7-Naphthyridinecarbonitriles 18221.5 1,7-Naphthyridinecarbaldehydes and Ketones 182Chapter 22 Primary Syntheses of 1,8-Naphthyridines 18322.1 From an Aliphatic Substrate 18322.2 From a Single Pyridine Substrate 18422.3 From a Pyridine Substrate and Synthon(s) 18722.4 From Other Heterocyclic Substrates 192Chapter 23 1,8-Naphthyridine, Alkyl-1,8-Naphthyridines, and Aryl-1,8-Naphthyridines 19723.1 1,8-Naphthyridine and Hydro Derivatives 19723.1.1 Preparation of 1,8-Naphthyridine 19723.1.2 Properties of 1,8-Naphthyridine 19823.1.3 1,8-Naphthyridine Complexes 19923.1.4 Reactions of 1,8-Naphthyridine 20023.2 Alkyl- and Aryl-1,8-Naphthyridines 20323.2.1 Preparation of Alkyl- and Aryl-1,8-Naphthyridines 20323.2.2 Reactions of Alkyl- and Aryl-1,8-Naphthyridines 205Chapter 24 Halogeno-1,8-Naphthyridines 20924.1 Preparation of Halogeno-1,8-Naphthyridines 20924.2 Reactions of Halogeno-1,8-Naphthyridines 214Chapter 25 Oxy-1,8-Naphthyridines 22125.1 1,8-Naphthyridinones and the Like 22125.1.1 Preparation of 1,8-Naphthyridinones and the Like 22125.1.2 Reactions of 1,8-Naphthyridinones and the Like 22425.2 Alkoxy- and Aryloxy-1,8-Naphthyridines 22725.3 1,8-Naphthyridine N-Oxides 228Chapter 26 Thio-1,8-Naphthyridines 23126.1 1,8-Naphthyridinethiones 23126.2 Alkylthio- and Arylthio-1,8-Naphthyridines 23226.3 1,8-Naphthyridine Sulfoxides and Sulfones 23226.4 1,8-Naphthyridinesulfonic Acids and the Like 233Chapter 27 Nitro-, Amino-, and Related 1,8-Naphthyridines 23527.1 Nitro-1,8-Naphthyridines 23527.1.1 Preparation of Nitro-1,8-Naphthyridines 23527.1.2 Reactions of Nitro-1,8-Naphthyridines 23727.2 Nitroso-1,8-Naphthyridines 23827.3 Amino-1,8-Naphthyridines 23827.3.1 Preparation of Amino-1,8-Naphthyridines 23827.3.2 Reactions of Amino-1,8-Naphthyridines 241Chapter 28 1,8-Naphthyridinecarboxylic Acids and Related Derivatives 24728.1 1,8-Naphthyridinecarboxylic Acids 24728.1.1 Preparation of 1,8-Naphthyridinecarboxylic Acids 24728.1.2 Reactions of 1,8-Naphthyridinecarboxylic Acids 24928.2 1,8-Naphthyridinecarbonyl Halides 25128.3 1,8-Naphthyridinecarboxylic Esters 25228.3.1 Preparation of 1,8-Naphthyridinecarboxylic Esters 25228.3.2 Reactions of 1,8-Naphthyridinecarboxylic Esters 25228.4 1,8-Naphthyridinecarboxamides 25428.4.1 Preparation of 1,8-Naphthyridinecarboxamides 25428.4.2 Reactions of 1,8-Naphthyridinecarboxamides 25528.5 1,8-Naphthyridinecarbonitriles 25728.6 1,8-Naphthyridinecarbaldehydes and Related Ketones 25728.6.1 Preparation of the Carbaldehydes and Ketones 25728.6.2 Reactions of the Carbaldehydes and Ketones 259Chapter 29 The 2,6-Naphthyridines 26129.1 Primary Syntheses of 2,6-Naphthyridines 26129.1.1 2,6-Naphthyridines by Cyclization of Pyridine Derivatives 26129.1.2 2,6-Naphthyridines by Cyclocondensation of a Pyridine Derivative with a Synthon 26329.1.3 2,6-Naphthyridines from Other Heterocyclic Substrates 26429.2 2,6-Naphthyridine and Alkyl-2,6-Naphthyridines 26529.2.1 Preparation of 2,6-Naphthyridine 26629.2.2 Properties of 2,6-Naphthyridine 26629.3 Halogeno-2,6-Naphthyridines 26729.3.1 Preparation of Halogeno-2,6-Naphthyridines 26729.3.2 Reactions of Halogeno-2,6-Naphthyridines 26829.4 Oxy-2,6-Naphthyridines 26929.5 Thio-2,6-Naphthyridines 27029.6 Nitro-, Amino-, and Related 2,6-Naphthyridines 27129.6.1 Preparation of Amino-2,6-Naphthyridines 27129.6.2 Reactions of Amino-2,6-Naphthyridines 27229.7 2,6-Naphthyridinecarboxylic Acids and Related Derivatives 272Chapter 30 The 2,7-Naphthyridines 27530.1 Primary Syntheses of 2,7-Naphthyridines 27530.1.1 2,7-Naphthyridines from Nonheterocyclic Precursors 27530.1.2 2,7-Naphthyridines by Cyclization of Pyridine Substrates 27730.1.3 2,7-Naphthyridines by Cyclocondensation of Pyridine Substrates with Synthons 27830.1.4 2,7-Naphthyridines from Other Heterocyclic Substrates 28030.2 2,7-Naphthyridine and Alkyl-2,7-Naphthyridines 28330.2.1 Preparation of 2,7-Naphthyridine 28330.2.2 Properties of 2,7-Naphthyridine 28330.2.3 Reactions of 2,7-Naphthyridine 28430.3 Halogeno-2,7-Naphthyridines 28530.3.1 Preparation of Halogeno-2,7-Naphthyridines 28630.3.2 Reactions of Halogeno-2,7-Naphthyridines 28730.4 Oxy-2,7-Naphthyridines 28930.5 Thio-2,7-Naphthyridines 29030.6 Nitro-, Amino-, and Related 2,7-Naphthyridines 29030.7 2,7-Naphthyridinecarboxylic Acids and Related Derivatives 29130.7.1 2,7-Naphthyridinecarboxylic Acids 29130.7.2 2,7-Naphthyridinecarboxylic Esters 29230.7.3 2,7-Naphthyridinecarboxamides and Carbonitriles 29330.7.4 2,7-Naphthyridinecarbaldehydes and Ketones 293References 295Appendix Tables of Simple Naphthyridines 337Table A.1 Alphabetical List of Simple 1,5-Naphthyridines 339Table A.2 Alphabetical List of Simple 1,6-Naphthyridines 348Table A.3 Alphabetical List of Simple 1,7-Naphthyridines 361Table A.4 Alphabetical List of Simple 1,8-Naphthyridines 366Table A.5 Alphabetical List of Simple 2,6-Naphthyridines 409Table A.6 Alphabetical List of Simple 2,7-Naphthyridines 411Index 415