The Chemistry of Heterocyclic Compounds, The Naphthyridines

THE NAPHTHYRIDINES......Page 1
Contents......Page 15
1.1 From a Single Aliphatic Substrate......Page 25
1.2.1 By Formation of the N1,C2-Bond......Page 26
1.2.2 By Formation of the C3,C4-Bond......Page 27
1.2.3 By Formation of the C4,C4a-Bond......Page 28
1.3.1 Where the Synthon Supplies One Atom......Page 29
1.3.2 Where the Synthon Supplies Two Atoms......Page 30
1.3.3 Where the Synthon Supplies Three Atoms......Page 31
1.4 From a Pyridine Substrate and Two Synthons......Page 33
1.5 From Other Heterocyclic Substrates......Page 34
2.1.1 Preparation of 1,5-Naphthyridine......Page 37
2.1.2 Properties of 1,5-Naphthyridine......Page 38
2.1.3 Reactions of 1,5-Naphthyridine......Page 40
2.2 Alkyl- and Aryl-1,5-Naphthyridines......Page 43
2.2.1 Preparation of Alkyl- and Aryl-1,5-Naphthyridines......Page 44
2.2.2 Reactions of Alkyl- and Aryl-1,5-Naphthyridines......Page 46
3.1.1 By Direct Halogenation......Page 49
3.1.2 By Halogenolysis of 1,5-Naphthyridinones or the Like......Page 50
3.1.3 By the Meissenheimer Reaction on 1,5-Naphthyridine N-Oxides......Page 53
3.2.1 Alcoholysis or Phenolysis of Halogeno-1, 5-Naphthyridines......Page 55
3.2.2 Aminolysis of Halogeno-1,5-Naphthyridines......Page 58
3.2.3 Other Reactions of Halogeno-1,5-Naphthyridines......Page 62
4.1 Tautomeric 1,5-Naphthyridinones and Extranuclear Hydroxy-1,5-Naphthyridines......Page 67
4.1.1 Preparation of Tautomeric 1,5-Naphthyridinones and the Like......Page 68
4.1.2 Reactions of Tautomeric 1,5-Naphthyridinones and the Like......Page 70
4.2 Alkoxy- and Aryloxy-1,5-Naphthyridines......Page 72
4.3 Nontautomeric 1,5-Naphthyridinones......Page 73
4.4 1,5-Naphthyridine N-Oxides......Page 74
CHAPTER 5 THIO-1,5-NAPHTHYRIDINES......Page 77
6.1.1 Preparation of Nitro-1,5-Naphthyridines......Page 79
6.1.2 Reactions of Nitro-1,5-Naphthyridines......Page 80
6.2 Amino- and (Substituted-Amino)-1,5-Naphthyridines......Page 81
6.2.2 Reactions of Amino-1,5-Naphthyridines......Page 82
7.1 1,5-Naphthyridinecarboxylic Acids......Page 85
7.2 1,5-Naphthyridinecarboxylic Esters......Page 88
7.3 1,5-Naphthyridinecarboxamides, Carbonitriles, Carbaldehydes, and Ketones......Page 89
8.1 By Condensation of Two or More Aliphatic Substrates/Synthons......Page 91
8.2 From a Single Pyridine Substrate......Page 93
8.3 From a Pyridine Substrate with One Synthon......Page 99
8.3.1 Where the Synthon Supplies One Ring Atom......Page 100
8.3.2 Where the Synthon Supplies Two Ring Atoms......Page 102
8.3.3 Where the Synthon Supplies Three or More Ring Atoms......Page 105
8.4 From a Pyridine Substrate with Two or More Synthons......Page 107
8.5 From Other Heterocyclic Systems......Page 108
9.1.1 Preparation of 1,6-Naphthyridine......Page 115
9.1.2 Properties of 1,6-Naphthyridine......Page 117
9.1.3 Reactions of 1,6-Naphthyridines......Page 118
9.2.1 Preparation of Alkyl- and Aryl-1,6-Naphthyridines......Page 121
9.2.2 Reactions of Alkyl- and Aryl-1,6-Naphthyridines......Page 123
10.1.1 By Direct Halogenation......Page 127
10.1.2 By Halogenolysis of 1,6-Naphthyridinones or the Like......Page 128
10.1.3 By Other Methods......Page 131
10.2.1 Alcoholysis or Phenolysis of Halogeno-1, 6-Naphthyridines......Page 132
10.2.2 Aminolysis of Halogeno-1,6-Naphthyridines......Page 134
10.2.3 Dehalogenation of Halogeno-1,6-Naphthyridines......Page 135
10.2.4 Other Reactions of Halogeno-1,6-Naphthyridines......Page 137
11.1 Tautomeric/Nontautomeric 1,6-Naphthyridinones and Extranuclear Hydroxy-1,6-Naphthyridines......Page 139
11.1.1 Preparation of 1,6-Naphthyridinones and the Like......Page 140
11.1.2 Reactions of 1,6-Naphthyridinones and the Like......Page 142
11.2 Alkoxy- and Acyloxy-1,6-Naphthyridines......Page 144
11.3 1,6-Naphthyridine N-Oxides......Page 145
CHAPTER 12 THIO-1,6-NAPHTHYRIDINES......Page 149
13.1.1 Preparation of Nitro-1,6-Naphthyridines......Page 151
13.1.2 Reactions of Nitro-1,6-Naphthyridines......Page 152
13.2 Amino- and (Substituted-Amino)-1,6-Naphthyridines......Page 153
13.2.1 Preparation of Amino-1,6-Naphthyridines......Page 154
13.2.2 Reactions of Amino-1,6-Naphthyridines......Page 155
14.1.1 Preparation of 1,6-Naphthyridinecarboxylic Acids......Page 159
14.1.2 Reactions of 1,6-Naphthyridinecarboxylic Acids......Page 161
14.3 1,6-Naphthyridinecarboxamides......Page 163
14.4 1,6-Naphthyridinecarbonitriles, Carbaldehydes, and Ketones......Page 165
15.2 From a Single Pyridine Substrate......Page 167
15.3 From a Pyridine Substrate with a Synthon......Page 171
15.4 From Other Heterocyclic Systems......Page 174
16.1.1 Preparation of 1,7-Naphthyridine......Page 177
16.1.2 Properties of 1,7-Naphthyridine......Page 178
16.1.3 Reactions of 1,7-Naphthyridine......Page 179
16.2.1 Preparation of Alkyl- and Aryl-1,7-Naphthyridines......Page 181
16.2.2 Reactions of Alkyl- and Aryl-1,7-Naphthyridines......Page 182
17.1 Preparation of Halogeno-1,7-Naphthyridines......Page 185
17.2 Reactions of Halogeno-1,7-Naphthyridines......Page 187
18.1.1 Preparation of 1,7-Naphthyridinones......Page 191
18.1.2 Reactions of 1,7-Naphthyridinones......Page 192
18.2 Alkoxy- and Acyloxy-1,7-Naphthyridines......Page 194
18.3 1,7-Naphthyridine N-Oxides......Page 195
CHAPTER 19 THIO-1,7-NAPHTHYRIDINES......Page 197
20.1 Nitro-1,7-Naphthyridines......Page 199
20.2 Amino-1,7-Naphthyridines......Page 200
21.1.1 Preparation of 1,7-Naphthyridinecarboxylic Acids......Page 203
21.1.2 Reactions of 1,7-Naphthyridinecarboxylic Acids......Page 204
21.5 1,7-Naphthyridinecarbaldehydes and Ketones......Page 206
22.1 From an Aliphatic Substrate......Page 207
22.2 From a Single Pyridine Substrate......Page 208
22.3 From a Pyridine Substrate and Synthon(s)......Page 211
22.4 From Other Heterocyclic Substrates......Page 216
23.1.1 Preparation of 1,8-Naphthyridine......Page 221
23.1.2 Properties of 1,8-Naphthyridine......Page 222
23.1.3 1,8-Naphthyridine Complexes......Page 223
23.1.4 Reactions of 1,8-Naphthyridine......Page 224
23.2.1 Preparation of Alkyl- and Aryl-1,8-Naphthyridines......Page 227
23.2.2 Reactions of Alkyl- and Aryl-1,8-Naphthyridines......Page 229
24.1 Preparation of Halogeno-1,8-Naphthyridines......Page 233
24.2 Reactions of Halogeno-1,8-Naphthyridines......Page 238
25.1.1 Preparation of 1,8-Naphthyridinones and the Like......Page 245
25.1.2 Reactions of 1,8-Naphthyridinones and the Like......Page 248
25.2 Alkoxy- and Aryloxy-1,8-Naphthyridines......Page 251
25.3 1,8-Naphthyridine N-Oxides......Page 252
26.1 1,8-Naphthyridinethiones......Page 255
26.3 1,8-Naphthyridine Sulfoxides and Sulfones......Page 256
26.4 1,8-Naphthyridinesulfonic Acids and the Like......Page 257
27.1.1 Preparation of Nitro-1,8-Naphthyridines......Page 259
27.1.2 Reactions of Nitro-1,8-Naphthyridines......Page 261
27.3.1 Preparation of Amino-1,8-Naphthyridines......Page 262
27.3.2 Reactions of Amino-1,8-Naphthyridines......Page 265
28.1.1 Preparation of 1,8-Naphthyridinecarboxylic Acids......Page 271
28.1.2 Reactions of 1,8-Naphthyridinecarboxylic Acids......Page 273
28.2 1,8-Naphthyridinecarbonyl Halides......Page 275
28.3.2 Reactions of 1,8-Naphthyridinecarboxylic Esters......Page 276
28.4.1 Preparation of 1,8-Naphthyridinecarboxamides......Page 278
28.4.2 Reactions of 1,8-Naphthyridinecarboxamides......Page 279
28.6.1 Preparation of the Carbaldehydes and Ketones......Page 281
28.6.2 Reactions of the Carbaldehydes and Ketones......Page 283
29.1.1 2,6-Naphthyridines by Cyclization of Pyridine Derivatives......Page 285
29.1.2 2,6-Naphthyridines by Cyclocondensation of a Pyridine Derivative with a Synthon......Page 287
29.1.3 2,6-Naphthyridines from Other Heterocyclic Substrates......Page 288
29.2 2,6-Naphthyridine and Alkyl-2,6-Naphthyridines......Page 289
29.2.2 Properties of 2,6-Naphthyridine......Page 290
29.3.1 Preparation of Halogeno-2,6-Naphthyridines......Page 291
29.3.2 Reactions of Halogeno-2,6-Naphthyridines......Page 292
29.4 Oxy-2,6-Naphthyridines......Page 293
29.5 Thio-2,6-Naphthyridines......Page 294
29.6.1 Preparation of Amino-2,6-Naphthyridines......Page 295
29.7 2,6-Naphthyridinecarboxylic Acids and Related Derivatives......Page 296
30.1.1 2,7-Naphthyridines from Nonheterocyclic Precursors......Page 299
30.1.2 2,7-Naphthyridines by Cyclization of Pyridine Substrates......Page 301
30.1.3 2,7-Naphthyridines by Cyclocondensation of Pyridine Substrates with Synthons......Page 302
30.1.4 2,7-Naphthyridines from Other Heterocyclic Substrates......Page 304
30.2.2 Properties of 2,7-Naphthyridine......Page 307
30.2.3 Reactions of 2,7-Naphthyridine......Page 308
30.3 Halogeno-2,7-Naphthyridines......Page 309
30.3.1 Preparation of Halogeno-2,7-Naphthyridines......Page 310
30.3.2 Reactions of Halogeno-2,7-Naphthyridines......Page 311
30.4 Oxy-2,7-Naphthyridines......Page 313
30.6 Nitro-, Amino-, and Related 2,7-Naphthyridines......Page 314
30.7.1 2,7-Naphthyridinecarboxylic Acids......Page 315
30.7.2 2,7-Naphthyridinecarboxylic Esters......Page 316
30.7.4 2,7-Naphthyridinecarbaldehydes and Ketones......Page 317
REFERENCES......Page 319
APPENDIX TABLES OF SIMPLE NAPHTHYRIDINES......Page 361
Table A.1 Alphabetical List of Simple 1,5-Naphthyridines......Page 363
Table A.2 Alphabetical List of Simple 1,6-Naphthyridines......Page 372
Table A.3 Alphabetical List of Simple 1,7-Naphthyridines......Page 385
Table A.4 Alphabetical List of Simple 1,8-Naphthyridines......Page 390
Table A.5 Alphabetical List of Simple 2,6-Naphthyridines......Page 433
Table A.6 Alphabetical List of Simple 2,7-Naphthyridines......Page 435
INDEX......Page 439