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Naphthyridines, Volume 63 [Hardback]

(University of Pittsburgh), (Princeton University), (Australian National University, Canberra)
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Each volume in this series deals with the synthesis, reactions, properties, structure, physical chemistry, and utility of compounds belonging to a specific ring system or class. This is the first book in the series devoted in its entirety to the six pyridopyridine ring systems, the naphthyridines. It covers the last 80 years of the literature, up through 2007. Brown (chemistry, Australian National University) covers the first four naphthyridines in seven chapters each, and other naphthyridine systems are covered in single long chapters. The appendix tables list all simple naphthyridines, along with an indication of their physical properties, which have been reported through 2006. Annotation ©2007 Book News, Inc., Portland, OR (booknews.com)

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.
Primary Syntheses of 1,5-Naphthyridines
1(12)
From a Single Aliphatic Substrate
1(1)
From a Single Pyridine Substrate
2(3)
By Formation of the N1, C2-Bond
2(1)
By Formation of the C3, C4-Bond
3(1)
By Formation of the C4, C4a-Bond
4(1)
From a Pyridine Substrate with One Synthon
5(4)
Where the Synthon Supplies One Atom
5(1)
Where the Synthon Supplies Two Atoms
6(1)
Where the Synthon Supplies Three Atoms
7(2)
From a Pyridine Substrate and Two Synthons
9(1)
From Other Heterocyclic Substrates
10(3)
1,5-Naphthyridine, Alkyl-1,5-Naphthyridines, and Aryl-1,5-Naphthyridines
13(12)
1,5-Naphthyridine
13(6)
Preparation of 1,5-Naphthyridine
13(1)
Properties of 1,5-Naphthyridine
14(2)
Reactions of 1,5-Naphthyridine
16(3)
Alkyl- and Aryl-1,5-Naphthyridines
19(6)
Preparation of Alkyl- and Aryl-1,5-Naphthyridines
20(2)
Reactions of Alkyl- and Aryl-1,5-Naphthyridines
22(3)
Halogeno-1,5-Naphthyridines
25(18)
Preparation of Halogeno-1,5-Naphthyridines
25(6)
By Direct Halogenation
25(1)
By Halogenolysis of 1,5-Naphthyridinones or the Like
26(3)
By the Meissenheimer Reaction on 1,5-Naphthyridine N-Oxides
29(2)
By Miscellaneous Procedures
31(1)
Reactions of Halogeno-1,5-Naphthyridines
31(12)
Alcoholysis or Phenolysis of Halogeno-1, 5-Naphthyridines
31(3)
Aminolysis of Halogeno-1,5-Naphthyridines
34(4)
Other Reactions of Halogeno-1,5-Naphthyridines
38(5)
Oxy-1,5-Naphthyridines
43(10)
Tautomeric 1,5-Naphthyridinones and Extranuclear Hydroxy-1,5-Naphthyridines
43(5)
Preparation of Tautomeric 1,5-Naphthyridinones and the Like
44(2)
Reactions of Tautomeric 1,5-Naphthyridinones and the Like
46(2)
Alkoxy- and Aryloxy-1,5-Naphthyridines
48(1)
Nontautomeric 1,5-Naphthyridinones
49(1)
1,5-Naphthyridine N-Oxides
50(3)
Thio-1,5-Naphthyridines
53(2)
Nitro-, Amino-, and Related 1,5-Naphthyridines
55(6)
Nitro-1,5-Naphthyridines
55(2)
Preparation of Nitro-1,5-Naphthyridines
55(1)
Reactions of Nitro-1,5-Naphthyridines
56(1)
Amino- and (Substituted-Amino)-1,5-Naphthyridines
57(4)
Preparation of Amino-1,5-Naphthyridines
58(1)
Reactions of Amino-1,5-Naphthyridines
58(3)
1,5-Naphthyridinecarboxylic Acids and Related Derivatives
61(6)
1,5-Naphthyridinecarboxylic Acids
61(3)
1,5-Naphthyridinecarboxylic Esters
64(1)
1,5-Naphthyridinecarboxamides, Carbonitriles, Carbaldehydes, and Ketones
65(2)
Primary Syntheses of 1,6-Naphthyridines
67(24)
By Condensation of Two or More Aliphatic Substrates/Synthons
67(2)
From a Single Pyridine Substrate
69(6)
From a Pyridine Substrate with One Synthon
75(8)
Where the Synthon Supplies One Ring Atom
76(2)
Where the Synthon Supplies Two Ring Atoms
78(3)
Where the Synthon Supplies Three or More Ring Atoms
81(2)
From a Pyridine Substrate with Two or More Synthons
83(1)
From Other Heterocyclic Systems
84(7)
1,6-Naphthyridine, Alkyl-1,6-Naphthyridines, and Aryl-1,6-Naphthyridines
91(12)
1,6-Naphthyridine
91(6)
Preparation of 1,6-Naphthyridine
91(2)
Properties of 1,6-Naphthyridine
93(1)
Reactions of 1,6-Naphthyridines
94(3)
Alkyl- and Aryl-1,6-Naphthyridines
97(6)
Preparation of Alkyl- and Aryl-1,6-Naphthyridines
97(2)
Reactions of Alkyl- and Aryl-1,6-Naphthyridines
99(4)
Halogeno-1,6-Naphthyridines
103(12)
Preparation of Halogeno-1,6-Naphthyridines
103(5)
By Direct Halogenation
103(1)
By Halogenolysis of 1,6-Naphthyridinones or the Like
104(3)
By Other Methods
107(1)
Reactions of Halogeno-1,6-Naphthyridines
108(7)
Alcoholysis or Phenolysis of Halogeno-1,6-Naphthyridines
108(2)
Aminolysis of Halogeno-1,6-Naphthyridines
110(1)
Dehalogenation of Halogeno-1,6-Naphthyridines
111(2)
Other Reactions of Halogeno-1,6-Naphthyridines
113(2)
Oxy-1,6-Naphthyridines
115(10)
Tautomeric/Nontautomeric 1,6-Naphthyridinones and Extranuclear Hydroxy-1,6-Naphthyridines
115(5)
Preparation of 1,6-Naphthyridinones and the Like
116(2)
Reactions of 1,6-Naphthyridinones and the Like
118(2)
Alkoxy- and Acyloxy-1,6-Naphthyridines
120(1)
1,6-Naphthyridine N-Oxides
121(4)
Thio-1,6-Naphthyridines
125(2)
Nitro-, Amino-, and Related 1,6-Naphthyridines
127(8)
Nitro-1,6-Naphthyridines
127(2)
Preparation of Nitro-1,6-Naphthyridines
127(1)
Reactions of Nitro-1,6-Naphthyridines
128(1)
Amino- and (Substituted-Amino)-1,6-Naphthyridines
129(6)
Preparation of Amino-1,6-Naphthyridines
130(1)
Reactions of Amino-1,6-Naphthyridines
131(4)
1,6-Naphthyridinecarboxylic Acids and Related Derivatives
135(8)
1,6-Naphthyridinecarboxylic Acids
135(4)
Preparation of 1,6-Naphthyridinecarboxylic Acids
135(2)
Reactions of 1,6-Naphthyridinecarboxylic Acids
137(2)
1,6-Naphthyridinecarboxylic Esters
139(1)
1,6-Naphthyridinecarboxamides
139(2)
1,6-Naphthyridinecarbonitriles, Carbaldehydes, and Ketones
141(2)
Primary Syntheses of 1,7-Naphthyridines
143(10)
From a Single Aliphatic Substrate
143(1)
From a Single Pyridine Substrate
143(4)
From a Pyridine Substrate with a Synthon
147(3)
From Other Heterocyclic Systems
150(3)
1,7-Naphthyridine, Alkyl-1,7-Naphthyridines, and Aryl-1,7-Naphthyridines
153(8)
1,7-Naphthyridine
153(4)
Preparation of 1,7-Naphthyridine
153(1)
Properties of 1,7-Naphthyridine
154(1)
Reactions of 1,7-Naphthyridine
155(2)
Alkyl- and Aryl-1,7-Naphthyridines
157(4)
Preparation of Alkyl- and Aryl-1,7-Naphthyridines
157(1)
Reactions of Alkyl- and Aryl-1,7-Naphthyridines
158(3)
Halogeno-1,7-Naphthyridines
161(6)
Preparation of Halogeno-1,7-Naphthyridines
161(2)
Reactions of Halogeno-1,7-Naphthyridines
163(4)
Oxy-1,7-Naphthyridines
167(6)
1,7-Naphthyridinones
167(3)
Preparation of 1,7-Naphthyridinones
167(1)
Reactions of 1,7-Naphthyridinones
168(2)
Alkoxy- and Acyloxy-1,7-Naphthyridines
170(1)
1,7-Naphthyridine N-Oxides
171(2)
Thio-1,7-Naphthyridines
173(2)
Nitro-, Amino-, and Related 1,7-Naphthyridines
175(4)
Nitro-1,7-Naphthyridines
175(1)
Amino-1,7-Naphthyridines
176(3)
1,7-Naphthyridinecarboxylic Acids and Related Derivatives
179(4)
1,7-Naphthyridinecarboxylic Acids
179(3)
Preparation of 1,7-Naphthyridinecarboxylic Acids
179(1)
Reactions of 1,7-Naphthyridinecarboxylic Acids
180(2)
1,7-Naphthyridinecarboxylic Esters
182(1)
1,7-Naphthyridinecarboxamides
182(1)
1,7-Naphthyridinecarbonitriles
182(1)
1,7-Naphthyridinecarbaldehydes and Ketones
182(1)
Primary Syntheses of 1,8-Naphthyridines
183(14)
From an Aliphatic Substrate
183(1)
From a Single Pyridine Substrate
184(3)
From a Pyridine Substrate and Synthon(s)
187(5)
From Other Heterocyclic Substrates
192(5)
1,8-Naphthyridine, Alkyl-1,8-Naphthyridines, and Aryl-1,8-Naphthyridines
197(12)
1,8-Naphthyridine and Hydro Derivatives
197(6)
Preparation of 1,8-Naphthyridine
197(1)
Properties of 1,8-Naphthyridine
198(1)
1,8-Naphthyridine Complexes
199(1)
Reactions of 1,8-Naphthyridine
200(3)
Alkyl- and Aryl-1,8-Naphthyridines
203(6)
Preparation of Alkyl- and Aryl-1,8-Naphthyridines
203(2)
Reactions of Alkyl- and Aryl-1,8-Naphthyridines
205(4)
Halogeno-1,8-Naphthyridines
209(12)
Preparation of Halogeno-1,8-Naphthyridines
209(5)
Reactions of Halogeno-1,8-Naphthyridines
214(7)
Oxy-1,8-Naphthyridines
221(10)
1,8-Naphthyridinones and the Like
221(6)
Preparation of 1,8-Naphthyridinones and the Like
221(3)
Reactions of 1,8-Naphthyridinones and the Like
224(3)
Alkoxy- and Aryloxy-1,8-Naphthyridines
227(1)
1,8-Naphthyridine N-Oxides
228(3)
Thio-1,8-Naphthyridines
231(4)
1,8-Naphthyridinethiones
231(1)
Alkylthio-and Arylthio-1,8-Naphthyridines
232(1)
1,8-Naphthyridine Sulfoxides and Sulfones
232(1)
1,8-Naphthyridinesulfonic Acids and the Like
233(2)
Nitro-, Amino-, and Related 1,8-Naphthyridines
235(12)
Nitro-1,8-Naphthyridines
235(3)
Preparation of Nitro-1,8-Naphthyridines
235(2)
Reactions of Nitro-1,8-Naphthyridines
237(1)
Nitroso-1,8-Naphthyridines
238(1)
Amino-1,8-Naphthyridines
238(9)
Preparation of Amino-1,8-Naphthyridines
238(3)
Reactions of Amino-1,8-Naphthyridines
241(6)
1,8-Naphthyridinecarboxylic Acids and Related Derivatives
247(14)
1,8-Naphthyridinecarboxylic Acids
247(4)
Preparation of 1,8-Naphthyridinecarboxylic Acids
247(2)
Reactions of 1,8-Naphthyridinecarboxylic Acids
249(2)
1,8-Naphthyridinecarbonyl Halides
251(1)
1,8-Naphthyridinecarboxylic Esters
252(2)
Preparation of 1,8-Naphthyridinecarboxylic Esters
252(1)
Reactions of 1,8-Naphthyridinecarboxylic Esters
252(2)
1,8-Naphthyridinecarboxamides
254(3)
Preparation of 1,8-Naphthyridinecarboxamides
254(1)
Reactions of 1,8-Naphthyridinecarboxamides
255(2)
1,8-Naphthyridinecarbonitriles
257(1)
1,8-Naphthyridinecarbaldehydes and Related Ketones
257(4)
Preparation of the Carbaldehydes and Ketones
257(2)
Reactions of the Carbaldehydes and Ketones
259(2)
The 2,6-Naphthyridines
261(14)
Primary Syntheses of 2,6-Naphthyridines
261(4)
2,6-Naphthyridines by Cyclization of Pyridine Derivatives
261(2)
2,6-Naphthyridines by Cyclocondensation of a Pyridine Derivative with a Synthon
263(1)
2,6-Naphthyridines from Other Heterocyclic Substrates
264(1)
2,6-Naphthyridine and Alkyl-2,6-Naphthyridines
265(2)
Preparation of 2,6-Naphthyridine
266(1)
Properties of 2,6-Naphthyridine
266(1)
Halogeno-2,6-Naphthyridines
267(2)
Preparation of Halogeno-2,6-Naphthyridines
267(1)
Reactions of Halogeno-2,6-Naphthyridines
268(1)
Oxy-2,6-Naphthyridines
269(1)
Thio-2,6-Naphthyridines
270(1)
Nitro-, Amino-, and Related 2,6-Naphthyridines
271(1)
Preparation of Amino-2,6-Naphthyridines
271(1)
Reactions of Amino-2,6-Naphthyridines
272(1)
2,6-Naphthyridinecarboxylic Acids and Related Derivatives
272(3)
The 2,7-Naphthyridines
275(20)
Primary Syntheses of 2,7-Naphthyridines
275(8)
2,7-Naphthyridines from Nonheterocyclic Precursors
275(2)
2,7-Naphthyridines by Cyclization of Pyridine Substrates
277(1)
2,7-Naphthyridines by Cyclocondensation of Pyridine Substrates with Synthons
278(2)
2,7-Naphthyridines from Other Heterocyclic Substrates
280(3)
2,7-Naphthyridine and Alkyl-2,7-Naphthyridines
283(2)
Preparation of 2,7-Naphthyridine
283(1)
Properties of 2,7-Naphthyridine
283(1)
Reactions of 2,7-Naphthyridine
284(1)
Halogeno-2,7-Naphthyridines
285(4)
Preparation of Halogeno-2,7-Naphthyridines
286(1)
Reactions of Halogeno-2,7-Naphthyridines
287(2)
Oxy-2,7-Naphthyridines
289(1)
Thio-2,7-Naphthyridines
290(1)
Nitro-, Amino-, and Related 2,7-Naphthyridines
290(1)
2,7-Naphthyridinecarboxylic Acids and Related Derivatives
291(4)
2,7-Naphthyridinecarboxylic Acids
291(1)
2,7-Naphthyridinecarboxylic Esters
292(1)
2,7-Naphthyridinecarboxamides and Carbonitriles
293(1)
2,7-Naphthyridinecarbaldehydes and Ketones
293(2)
REFERENCES
295(42)
APPENDIX TABLES OF SIMPLE NAPHTHYRIDINES
337(78)
Table A.1 Alphabetical List of Simple 1,5-Naphthyridines
339(9)
Table A.2 Alphabetical List of Simple 1,6-Naphthyridines
348(13)
Table A.3 Alphabetical List of Simple 1,7-Naphthyridines
361(5)
Table A.4 Alphabetical List of Simple 1,8-Naphthyridines
366(43)
Table A.5 Alphabetical List of Simple 2,6-Naphthyridines
409(2)
Table A.6 Alphabetical List of Simple 2,7-Naphthyridines
411(4)
Index 415


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.