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Tables of Contents for Heterocyclic Chemistry
Chapter/Section Title
Page #
Page Count
Preface
xii
Introduction to the fourth edition
xiii
Definitions of abbreviations
xvi
Structures and spectroscopic properties of aromatic heterocycles
1
15
Carbocyclic aromatic systems
1
2
Structure of six-membered heteroaromatic systems
3
2
Structure of five-membered heteroaromatic systems
5
2
Structures of bicyclic heteroaromatic compounds
7
1
Tautomerism in heterocyclic systems
7
1
Mesoionic systems
8
1
Some spectroscopic properties of some heteroaromatic systems
8
8
References
14
2
Reactivity of aromatic heterocycles
16
37
Electrophilic addition at nitrogen
16
1
Electrophilic substitution at carbon
17
3
Nucleophilic substitution at carbon
20
3
Radical substitution at carbon
23
3
Deprotonation of N-hydrogen
26
1
Organometallic derivatives
26
14
Palladium-catalysed reactions
40
6
Oxidation and reduction of heterocyclic rings
46
1
Bioprocesses in heterocyclic chemistry
46
7
References
47
6
Synthesis of aromatic heterocycles
53
10
Reaction types most frequently used in heterocyclic ring synthesis
53
1
Typical reactant combinations
54
2
Summary
56
1
Electrocyclic processes in heterocyclic ring synthesis
57
1
Nitrenes in heterocyclic ring synthesis
58
1
ortho-Quinodimethanes in heterocyclic compound synthesis
59
4
References
61
2
Typical reactivity of pyridines, quinolines and isoquinolines
63
8
Pyridines: reactions and synthesis
71
50
Reactions with electrophilic reagents
72
5
Reactions with oxidising agents
77
1
Reactions with nucleophilic reagents
78
2
Reactions with bases
80
1
Reactions of C-metallated pyridines
81
3
Reactions with radical reagents; reactions of pyridyl radicals
84
2
Reactions with reducing agents
86
1
Electrocyclic reactions (ground state)
86
1
Photochemical reactions
87
1
Oxy- and aminopyridines
88
5
Alkylpyridines
93
1
Pyridine aldehydes, ketones, carboxylic acids and esters
94
1
Quaternary pyridinium salts
95
5
Pyridine N-oxides
100
3
Synthesis of pyridines
103
18
Exercises for chapter 5
110
2
References
112
9
Quinolines and isoquinolines: reactions and synthesis
121
27
Reactions with electrophilic reagents
122
1
Reactions with oxidising agents
123
1
Reactions with nucleophilic reagents
123
3
Reactions with bases
126
1
Reactions of C-metallated quinolines and isoquinolines
126
1
Reactions with radical reagents
127
1
Reactions with reducing agents
127
1
Electrocyclic reactions (ground state)
128
1
Photochemical reactions
128
1
Oxyquinolines and -isoquinolines
128
2
Aminoquinolines and -isoquinolines
130
1
Alkylquinolines and -isoquinolines
130
1
Quinoline and isoquinoline carboxylic acids and esters
130
1
Quaternary quinolinium salts
131
1
Quinoline and isoquinoline N-oxides
132
1
Synthesis of qinolines and isoquinolines
133
15
Exercises for chapter 6
142
1
References
143
5
Typical reactivity of pyrylium and benzopyrylium ions, pyrones and benzopyrones
148
3
Pyryiliums, 2- and 4-pyrones: reations and synthesis
151
19
Reactions of pyrylium cations
151
5
2-Pyrones and 4 -pyrones (2H-pyran-2-ones and 4H-pyran-4-ones; α-pyrones and &gama;-pyrones)
156
4
Synthesis of pyryliums
160
2
Synthesis of 2-pyrones
162
2
Synthesis of 4-pyrones
164
6
Exercises for chapter 8
165
1
References
166
4
Benzopyryliums, benzopyrones: reactions and synthesis
170
20
Reactions of benzopyryliums
170
3
Benzopyrones (chromones, coumarins, and isocoumarins)
173
6
Synthesis of benzopyryliums, chromones, coumarins and isocoumarins
179
11
Exercises for chapter 9
186
1
References
186
4
Typical reactivity of the diazines: pyridazine, pyrimidine and pyrazine
190
4
The diazines: pyridazine, pyrimidine, and pyrazine: reactions and synthesis
194
39
Reactions with electrophilic reagents
196
2
Reactions with oxidising agents
198
1
Reactions with nucleophilic reagents
198
3
Reactions with bases
201
1
Reactions of C-metallated diazines
202
2
Reactions with reducing agents
204
1
Reactions with radical reagents
204
1
Electrocyclic reactions
204
1
Diazine N-oxides
205
1
Oxydiazines
206
8
Aminodiazines
214
1
Alkyldiazines
215
1
Quaternary azinium salts
215
1
Synthesis of diazines
216
8
Pteridines
224
9
Exercises for chapter 11
225
1
References
226
7
Typical reactivity of pyrroles, thiophenes, and furans
233
4
Pyrroles: reactions and synthesis
237
36
Reactions with electropilic reagents
238
8
Reactions with oxidising agents
246
1
Reactions with nucleophilic reagents
246
1
Reactions with bases
246
1
Reactions of N-metallated pyrroles
247
1
Reactions of C-metallated pyrroles
248
1
Reactions with radical reagents
249
1
Reactions with reducing agents
250
1
Electrocyclic reactions (ground state)
250
2
Reactions with carbenes and carbenoids
252
1
Photochemical reactions
252
1
Pyrryl-C-X compounds
252
1
Pyrrole aldehydes and ketones
253
1
Pyrrole carboxylic acids
253
1
Pyrrole carboxylic acid esters
254
1
Halopyrroles
254
1
Oxy- and aminopyrroles
254
1
Synthesis of pyrroles
255
18
Exercises for chapter 13
265
1
References
266
7
Thiophenes: reactions and synthesis
273
23
Reactions with electrophilic reagents
273
5
Reactions with oxidising agents
278
1
Reactions with nucleophilic reagents
279
1
Reactions with bases
279
1
Reactions of C-metallated thiophenes
280
2
Reactions with radical reagents
282
1
Reactions with reducing agents
283
1
Electrocyclic reactions (ground state)
283
1
Photochemical reactions
284
1
Thiophene-C-X compounds: thenyl derivatives
284
1
Thiophene aldehydes and ketones, and carboxylic acids and esters
285
1
Oxy- and aminothiophenes
285
1
Synthesis of thiophenes
286
10
Exercises for chapter 14
290
1
References
291
5
Furans: reactions and synthesis
296
23
Reactions with electrophilic reagents
296
4
Reactions with oxidising agents
300
1
Reactions with nucleophilic reagents
300
1
Reactions with bases
301
1
Reactions of C-metallated furans
302
1
Reactions with radical reagents
303
1
Reactions with reducing agents
303
1
Electrocyclic reactions (ground state)
303
2
Photochemical reactions
305
1
Furyl-C-X compounds; side-chain properties
305
1
Furan carboxylic acids and esters
306
1
Oxy- and aminofurans
306
2
Synthesis of furans
308
11
Exercises for chapter 15
313
1
References
314
5
Typical reactivity of indoles, benzo[b]thiophenes, benzo[b]furans, isoindoles, benzo[c]thiophenes and isobenzofurans
319
5
Indoles: reactions and synthesis
324
56
Reactions with electrophilic reagents
325
11
Reactions with oxidising agents
336
1
Reactions with nucleophilic reagents (see also section 17.14.4)
337
1
Reactions with bases
337
1
Reactions of N-metallated indoles
338
1
Reactions of C-metallated indoles
339
2
Reactions with radicals
341
1
Reactions with reducing agents
342
1
Reactions with carbenes
342
1
Electrocyclic and photochemical reactions
343
2
Alkylindoles
345
1
Reactions of indolyl-C-X compounds
345
1
Indole carboxylic acids
346
1
Oxyindoles
347
3
Aminoindoles
350
1
Azaindoles
351
2
Synthesis of indoles
353
27
Exercises for chapter 17
370
1
References
371
9
Benzo[b]thiophenes and benzo[b]furans: reactions and synthesis
380
12
Reactions with electrophilic reagents
380
2
Reactions with nuleophilic reagents
382
1
Reactions with bases; reactions of C-metallated benzo[b]thiophenes and benzo[b]furans
382
1
Reactions with oxidising and reducing agents
383
1
Electrocyclic reactions
384
1
Oxy- and amino-benzothiophenes and -benzofurans
384
1
Synthesis of benzo[b]thiophenes and benzo[b]furans
384
8
Exercises for chapter 18
389
1
References
389
3
Isoindoles, benzo[c]thiophenes and isobenzofurans: reactions and synthesis
392
7
Reactions with electrophilic reagents
392
1
Electrocyclic reactions
393
1
Phthalocyanines
393
1
Synthesis of isoindoles, benzo[c]thiophenes, and isobenzofurans
394
5
Exercises for chapter 19
397
1
References
397
2
Typical reactivity of 1,3- and 1,2-azoles
399
3
1,3-Azoles: imidazoles, thiazoles, and oxazoles: reactions and synthesis
402
29
Reactions with electrophilic reagents
403
5
Reactions with oxidising agents
408
1
Reactions with nucleophilic reagents
408
1
Reactions with bases
409
1
Reactions of N-metallated imidazoles
409
1
Reactions of C-metallated 1,3-azoles
410
2
Reactions with radical reagents
412
1
Reactions with reducing agents
412
1
Electrocyclic reactions
412
2
Alkyl-1,3-azoles
414
1
Quaternary 1,3-azolium salts
414
2
Oxy- and amino-1,3-azoles
416
2
1,3-Azole N-oxides
418
1
Synthesis of 1,3-azoles
418
13
Exercises for chapter 21
424
1
References
425
6
1,2-Azoles: pyrazoles, isothiazoles, isoxazoles: reactions and synthesis
431
18
Reactions with electrophilic reagents
432
2
Reactions with oxidising agents
434
1
Reactions with nucleophilic reagents
434
1
Reactions with bases
434
1
Reactions of N-metallated pyrazoles
435
1
Reactions of C-metallated 1,2-azoles
435
1
Reactions with radicals
436
1
Reactions with reducing agents
436
1
Electrocyclic reactions
437
1
Alkyl-1,2-azoles
438
1
Quaternary 1,2-azolium salts
438
1
Oxy- and amino-1,2-azoles
439
1
Synthesis of 1,2-azoles
440
9
Exercises for chapter 22
444
1
References
445
4
Benzanellated azoles: reactions and synthesis
449
12
Reactions with electrophilic reagents
449
1
Reactions with nucleophilic reagents
450
1
Reactions with bases
451
1
Reactions of C-metallated derivatives
451
1
Reactions with reducing agents
452
1
Electrocyclic reactions
452
1
Quaternary salts
453
1
Oxy- and amino-1,3-azoles
453
1
Synthesis
454
7
References
458
3
Purines: reactions and synthesis
461
28
Nucleic acids, nucleosides, and nucleotides
463
1
Reactions with electrophilic reagents
464
5
Reactions with radical reagents
469
1
Reactions with oxidising agents
469
1
Reactions with reducing agents
469
1
Reactions with nucleophilic reagents
470
2
Reactions with bases
472
1
Reactions of N-metallated purines
473
1
Reactions of C-metallated purines
473
2
Oxy- and aminopurines
475
4
Alkylpurines
479
1
Purine carboxylic acids
479
1
Synthesis of purines
479
10
Exercises for chapter 24
485
1
References
485
4
Heterocycles containing a ring-junction nitrogen
489
15
Indolizines
489
3
Aza-indolizines
492
6
Quinolizinium and related systems
498
1
Pyrrolizines and related systems
499
1
Cyclazines
500
4
Exercises for chapter 25
500
1
References
501
3
Heterocycles containing more than two hetero atoms
504
22
Five-membered rings
504
12
Six-membered rings
516
4
Benzotriazoles
520
6
Exercises for chapter 26
522
1
References
522
4
Saturated and partially unsaturated heterocyclic compounds: reactions and synthesis
526
17
Five- and six-membered rings
527
3
Three-membered rings
530
4
Four-membered rings
534
1
Metallation
535
1
Ring synthesis
536
7
References
540
3
Heterocycles at work
543
8
Solid phase reactions
543
2
Heterocycles in the pharmaceutical industry: large scale heterocyclic synthesis
545
1
Electronic applications
546
5
References
549
2
Appendix: answers to exercises
551
8
Chapter 5
551
1
Chapter 6
552
1
Chapter 8
552
1
Chapter 9
553
1
Chapter 11
553
1
Chapter 13
553
1
Chapter 14
554
1
Chapter 15
554
1
Chapter 17
554
1
Chapter 18
555
1
Chapter 19
555
1
Chapter 21
556
1
Chapter 22
556
1
Chapter 24
556
1
Chapter 25
557
1
Chapter 26
557
2
Index
559