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.
Table of Contents:
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
About the Author :
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.
