Heterocyclic chemistry:
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| Main Authors: | , |
|---|---|
| Format: | Book |
| Language: | English |
| Published: |
Chichester
Wiley
2010
|
| Edition: | 5. ed., 1. publ. |
| Subjects: | |
| Online Access: | Inhaltsverzeichnis Klappentext |
| Item Description: | Hier auch später erschienene, unveränderte Nachdrucke |
| Physical Description: | XXVII, 689 S. graph. Darst. |
| ISBN: | 9781405133005 9781405193658 |
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| 100 | 1 | |a Joule, John A. |e Verfasser |0 (DE-588)1031833455 |4 aut | |
| 245 | 1 | 0 | |a Heterocyclic chemistry |c John A. Joule ; Keith Mills |
| 250 | |a 5. ed., 1. publ. | ||
| 264 | 1 | |a Chichester |b Wiley |c 2010 | |
| 300 | |a XXVII, 689 S. |b graph. Darst. | ||
| 336 | |b txt |2 rdacontent | ||
| 337 | |b n |2 rdamedia | ||
| 338 | |b nc |2 rdacarrier | ||
| 500 | |a Hier auch später erschienene, unveränderte Nachdrucke | ||
| 650 | 4 | |a Heterocyclic chemistry | |
| 650 | 0 | 7 | |a Heterocyclische Verbindungen |0 (DE-588)4159726-6 |2 gnd |9 rswk-swf |
| 689 | 0 | 0 | |a Heterocyclische Verbindungen |0 (DE-588)4159726-6 |D s |
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| 700 | 1 | |a Mills, Keith |e Verfasser |0 (DE-588)172914167 |4 aut | |
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| 856 | 4 | 2 | |m Digitalisierung UB Bayreuth |q application/pdf |u http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=018716927&sequence=000004&line_number=0002&func_code=DB_RECORDS&service_type=MEDIA |3 Klappentext |
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| adam_text | Contents
Preface
to the Fifth Edition
xix
P.I Hazards
xxi
P.2 How to Use This Textbook
xxi
Acknowledgements
xxii
References
xxii
Web Site
xxii
Biography
xxiii
Definitions of Abbreviations
xxv
1
Heterocyclic Nomenclature
1
2
Structures and
Spectroscopie
Properties of Aromatic Heterocycies
5
2.1
Carbocyclic Aromatic Systems
5
2.1.1
Structures of Benzene and Naphthalene
5
2.1.2
Aromatic Resonance Energy
6
2.2
Structure of Six-Membered Heteroaromatic Systems
7
2.2.1
Structure of
Pyridine
7
2.2.2
Structure of Diazines
7
2.2.3
Structures of Pyridinium and Related Cations
8
2.2.4
Structures of Pyridones and Pyrones
8
2.3
Structure of Five-Membered Heteroaromatic Systems
9
2.3.1
Structure of Pyrrole
9
2.3.2
Structures of Thiophene and
Furan
10
2.3.3
Structures of Azoles
10
2.3.4
Structures of Pyrryl and Related Anions
11
2.4
Structures of Bicyclic Heteroaromatic Compounds
11
2.5
Tautomerism in Heterocyclic Systems
12
2.6
Mesoionic Systems
12
2.7
Some
Spectroscopie
Properties of Some Heteroaromatic Systems
13
2.7.1
Ultraviolet/Visible (Electronic) Spectroscopy
13
2.7.2
Nuclear Magnetic Resonance (NMR) Spectroscopy
14
References
17
3
Substitutions of Aromatic Heterocycies
19
3.1
Electrophilic Addition at Nitrogen
19
3.2
Electrophilic Substitution at Carbon
20
3.2.1
Aromatic Electrophilic Substitution: Mechanism
20
3.2.2
Six-Membered Heterocycies
21
3.2.3
Five-Membered Heterocycies
22
vi
Contents
3.3
Nucleophilic
Substitution
at Carbon
3.3.1
Aromatic Nucleophilic Substitution: Mechanism
3.3.2
Six-Membered Heterocycles
3.3.3
Vicarious Nucleophilic Substitution (VNS Substitution)
3.4
Radical Substitution at Carbon
3.4.1
Reactions of Heterocycles with Nucleophilic Radicals
3.4.2
Reactions with Electrophilic Radicals
3.5
Deprotonation of N-Hy
drogen
3.6
Oxidation and Reduction of Heterocyclic Rings
3.7
огѓЛо
-Quinodimeťhanes
in Heterocyclic Compound Synthesis
References
24
24
24
26
27
27
30
30
31
31
33
4
Organometallic Heterocyclic Chemistry
4.1
Preparation and Reactions of Organometallic Compounds
4.1
1.1
Lithium
4.1.2
Magnesium
4.1
1.3
Zinc
4.1
1.4
Copper
4.1
1.5
Boron
4.1
1.6
Silicon and Tin
4.
1.7
Mercury
4.
і
1.8
Palladium
4.1
1.9
Side-Chain Metallation ( Lateral Metallation )
Ml Transition Metal-Catalysed Reactions
4.2.1
Basic Palladium Processes
4.2.2
Catalysts
4.2.3
The Electrophilic Partner; The Halides/Leaving Groups
4.2.4
Cross-Coupling Reactions
4.2.5
The Nucleophilic (Organometallic) Partner
4.2.6
Other Nucleophiles
4.2.7
The Ring Systems in Cross-Coupling Reactions
4.2.8
Organometallic Selectivity
4.2.9
Direct
C
-Н
Arylation
4.2.10
N-Arylation
4.2.11
Heck Reactions
4.2.12
Carbonylation Reactions
References
37
37
37
45
47
48
48
52
54
54
54
56
56
59
61
64
65
70
71
77
79
83
87
89
90
5
Methods in Heterocyclic Chemistry
5.1
Solid-Phase Reactions and Related Methods
5.2
5.3
5.4
5.1.1
5.1.2
5.1.3
5.1.4
5.1.5
References
Solid-Phase Reactions
Solid-Supported Reagents and Scavengers
Solid-Phase Extraction
(SPE)
Soluble Polymer-Supported Reactions
Phase Tags
Microwave Heating
Flow Reactors
Hazards: Explosions
97
97
97
99
100
100
101
103
104
105
105
Contents
vii
6
Ring Synthesis of Aromatic Heterocycles
107
6.1
Reaction Types Most Frequently Used in Heterocyclic Ring Synthesis
107
6.2
Typical Reactant Combinations
108
6.2.1
Typical Ring Synthesis of a Pyrrole Involving Only C-Heteroatom Bond
Formation
108
6.2.2
Typical Ring Synthesis of
a Pyridine
Involving Only C-Heteroatom Bond
Formation
109
6.2.3
Typical Ring Syntheses Involving C-Heteroatom
C
-С
Bond Formations
109
6.3
Summary
111
6.4
Electrocyclic Processes in Heterocyclic Ring Synthesis
112
6.5
Nitrenes in Heterocyclic Ring Synthesis
113
6.6
Palladium Catalysis in the Synthesis of Benzo-Fused Heterocycles
113
References
114
7
Typical Reactivity of Pyridines, Quinolines and Isoquinolines
115
8
Pyridines: Reactions and Synthesis
125
8.1
Reactions with Electrophilic Reagents
125
8.1.1
Addition to Nitrogen
125
8.1.2
Substitution at Carbon
128
8.2
Reactions with Oxidising Agents
130
8.3
Reactions with Nucleophilic Reagents
131
8.3.1
Nucleophilic Substitution with Hydride Transfer
131
8.3.2
Nucleophilic Substitution with Displacement of Good Leaving Groups
133
8.4
Metallation and Reactions of C-Metallated-Pyridines
134
8.4.1
Direct Ring
C
-Н
Metallation
134
8.4.2
Metal-Halogen Exchange
137
8.5
Reactions with Radicals; Reactions of Pyridyl Radicals
138
8.5.1
Halogenation
138
8.5.2
Carbon Radicals
138
8.5.3
Dimerisation
138
8.5.4
Pyridinyl Radicals
139
8.6
Reactions with Reducing Agents
139
8.7
Electrocyclic Reactions (Ground State)
140
8.8
Photochemical Reactions
140
8.9
Oxy- and Amino-Pyridines
141
8.9.1
Structure
141
8.9.2
Reactions of Pyridones
142
8.9.3
Reactions of Amino-Pyridines
144
8.10
Alkyl-Pyridines
146
8.11
Pyridine
Aldehydes, Ketones, Carboxylic Acids and Esters
148
8.12
Quaternary Pyridinium Salts
148
8.12.1
Reduction and Oxidation
148
8.12.2
Organometallic and Other Nucleophilic Additions
150
8.12.3
Nucleophilic Addition Followed by Ring Opening
152
8.12.4
Cyclisations Involving an
α
-Position or an
α
-Substituent
153
8.12.5
N-Dealkylation
153
8.13
Pyridine
N-oxides
153
8.13.1
Electrophilic Addition and Substitution
154
8.13.2
Nucleophilic Addition and Substitution
155
8.13.3
Addition of Nucleophiles then Loss of Oxide
155
viii Contents
8.14
Synthesis of Pyridines
156
8.14.1
Ring Synthesis 156
8.14.2
Examples of Notable Syntheses of
Pyridine
Compounds
165
Exercises
166
References 168
9
Quinolines and Isoquinolines: Reactions and Synthesis
177
9.1
Reactions with Electrophilic Reagents
177
9.1.1
Addition to Nitrogen
177
9.1.2
Substitution at Carbon
177
9.2
Reactions with Oxidising Agents
179
9.3
Reactions with Nucleophilic Reagents
179
9.3.1
Nucleophilic Substitution with Hydride Transfer
179
9.3.2
Nucleophilic Substitution with Displacement of Good Leaving Groups
180
9.4
Metallation and Reactions of C-Metallated Quinolines and Isoquinolines
181
9.4.1
Direct Ring
C
-Н
Metallation
181
9.4.2
Metal-Halogen Exchange
182
9.5
Reactions with Radicals
182
9.6
Reactions with Reducing Agents
183
9.7
Electrocyclic Reactions (Ground State)
183
9.8
Photochemical Reactions
183
9.9
Oxy-Quinolines and Oxy-Isoquinolines
183
9.10
Amino-Quinolines and Amino-Isoquinolines
185
9.11
Alkyl-Quinolines and Alkyl-Isoquinolines
185
9.12
Quinoline and Isoquinoline Carboxylic Acids and Esters
185
9.13
Quaternary Quinolinium and Isoquinolinium Salts
186
9.14
Quinoline and Isoquinoline N-Oxides
188
9.15
Synthesis of Quinolines and Isoquinolines
188
9.15.1
Ring Syntheses
188
9.15.2
Examples of Notable Syntheses of Quinoline and Isoquinoline Compounds
198
Exercises
199
References
200
10
Typical Reactivity of Pyrylium and Benzopyrylium Ions, Pyrones and Benzopyrones
205
11
Pyryliums,
2-
and 4-Pyrones: Reactions and Synthesis
209
11.1
Reactions of Pyrylium Cations
209
11.1.1
Reactions with Electrophilic Reagents
209
11.1.2
Addition Reactions with Nucleophilic Reagents
210
11.1.3
Substitution Reactions with Nucleophilic Reagents
212
11.1.4
Reactions with Radicals
212
11.1.5
Reactions with Reducing Agents
212
11.1.6
Photochemical Reactions
212
11.1.7
Reactions with Dipolarophiles;
Cycloadditions
213
11.1.8
Alkyl-Pyryliums
213
11.2
2-Pyrones and 4-Pyrones
(2Я-Ругап-2-опе8
and 4#-Pyran-4-ones; a- and
γ
-Pyrones)
214
11.2.1
Structure of Pyrones
214
11.2.2
Reactions of Pyrones
214
Contents ix
11.3
Synthesis of
Pyryliums 218
11.3.1
From US-Dicarbonyl Compounds
218
11.3.2
Alkene Acylation
219
11.3.3
From 1,3-Dicarbonyl Compounds and Ketones
220
11.4
Synthesis of 2-Pyrones
220
11.4.1
From l^-Ketoialdehydo)-Acids and Carbonyl Compounds
220
11.4.2
Other Methods
221
11.5
Synthesis of 4-Pyrones
222
Exercises
224
References
225
12
Benzopyryliums and Benzopyrones: Reactions and Synthesis
229
12.1
Reactions of Benzopyryliums
229
12.1.1
Reactions with Electrophilic Reagents
229
12.1.2
Reactions with Oxidising Agents
230
12.1.3
Reactions with Nucleophilic Reagents
230
12.1.4
Reactions with Reducing Agents
231
12.1.5
Alky 1-Benzopyry Hums
231
12.2
Benzopyrones (Chromones, Coumarins and Isocoumarins)
232
12.2.1
Reactions with Electrophilic Reagents
232
12.2.2
Reactions with Oxidising Agents
232
12.2.3
Reactions with Nucleophilic Reagents
233
12.3
Synthesis of Benzopyryliums, Chromones, Coumarins and Isocoumarins
237
12.3.1
Ring Synthesis of
1
-Benzopyryliums
237
12.3.2
Ring Synthesis of Coumarins
238
12.3.3
Ring Synthesis of Chromones
240
12.3.4
Ring Synthesis of 2-Benzopyryliums
242
12.3.5
Ring Synthesis of Isocoumarins
243
12.3.6
Notable Examples of Benzopyrylium and Benzopyrone Syntheses
243
Exercises
244
References
245
13
Typical Reactivity of the Diazine: Pyridazine, Pyrimidine and Pyrazine
249
14
The Diazines: Pyridazine, Pyrimidine, and Pyrazine: Reactions and Synthesis
253
14.1
Reactions with Electrophilic Reagents
253
14.1.1
Addition at Nitrogen
253
14.1.2
Substitution at Carbon
255
14.2
Reactions with Oxidising Agents
255
14.3
Reactions with Nucleophilic Reagents
255
14.3.1
Nucleophilic Substitution with Hydride Transfer
256
14.3.2
Nucleophilic Substitution with Displacement of Good Leaving Groups
256
14.4
Metallation and Reactions of C-Metallated Diazines
259
14.4.1
Direct Ring
C
-Н
Metallation
259
14.4.2
Metal-Halogen Exchange
260
14.5
Reactions with Reducing Agents
261
14.6
Reactions with Radicals
261
14.7
Electrocyclic Reactions
261
14.8
Diazine W-Oxides
262
χ
Contents
14.9 Oxy-Diazines 263
14.9.1
Structure
of
Oxy-Diazines 263
14.9.2
Reactions of Oxy-Diazines 264
14.10 Amino-Diazines 271
14.11 Alkyl-Diazines 272
14.12
Quaternary Diazinium Salts
273
14.13
Synthesis of
Diazines 273
14.13.1 Pyridazines 274
14.13.2 Pyrimidines 275
14.13.3 Pyrazines 279
14.13.4 Notable
Syntheses of
Diazines 281
14.14 Pteridines 282
Exercises
283
References
284
15
Typical Reactivity of Pyrroles,
Furans
and Thiophenes
289
16
Pyrroles: Reactions and Synthesis
295
16.1
Reactions with Electrophilic Reagents
295
16.1.1
Substitution at Carbon
296
16.2
Reactions with Oxidising Agents
303
16.3
Reactions with Nucleophilic Reagents
303
16.4
Reactions with Bases
304
16.4.1
Deprotonation of N-Hy
drogen
and Reactions of Pyrryl Anions
304
16.4.2
Lithium, Sodium, Potassium and Magnesium Derivatives
304
16.5
C-Metallation and Reactions of C-Metallated Pyrroles
305
16.5.1
Direct Ring
C
-Н
Metallation
305
16.5.2
Metal-Halogen Exchange
305
16.6
Reactions with Radicals
306
16.7
Reactions with Reducing Agents
306
16.8
Electrocyclic Reactions (Ground State)
307
16.9
Reactions with Carbenes and Carbenoids
308
16.10
Photochemical Reactions
308
16.11
Pyrryl-C-X Compounds
309
16.12
Pyrrole Aldehydes and Ketones
309
16.13
Pyrrole Carboxylic Acids
309
16.14
Pyrrole Carboxylic Acid Esters
310
16.15
Oxy-and Amino-Pyrroles
310
16.15.1
2-Oxy-Pyrroles
310
16.15.2
3-Oxy-Pyrroles
311
16.15.3
Amino-Pyrroles
311
16.16
Synthesis of Pyrroles
311
16.16.1
Ring Synthesis
311
16.16.2
Some Notable Syntheses of Pyrroles
317
Exercises
319
References
320
17
Thiophenes: Reactions and Synthesis
325
17.1
Reactions with Electrophilic Reagents
325
17.1.1
Substitution at Carbon
325
17.1.2
Addition at Sulfur
329
Contents xi
17.2
Reactions with Oxidising Agents
330
17.3
Reactions with Nucleophilic Reagents
330
17.4
Metallation and Reactions of C-Metallated Thiophenes
331
17.4.1
Direct Ring
C
-Н
Metallation
331
17.4.2
Metal—Halogen Exchange
331
17.5
Reactions with Radicals
333
17.6
Reactions with Reducing Agents
333
17.7
Electrocyclic Reactions (Ground State)
333
17.8
Photochemical Reactions
334
17.9
Thiophene-C-X Compounds: Thenyl Derivatives
334
17.10
Thiophene Aldehydes and Ketones, and Carboxylic Acids and Esters
335
17.11
Oxy-and Amino-Thiophenes
335
17.11.1
Oxy-Thiophenes
335
17.11.2
Amino-Thiophenes
336
17.12
Synthesis of Thiophenes
336
17.12.1
Ring Synthesis
336
17.12.2
Examples of Notable Syntheses of Thiophene Compounds
340
Exercises
342
References
342
18
Furans:
Reactions and Synthesis
347
18.1
Reactions with Electrophilic Reagents
347
18.1.1
Substitution at Carbon
347
18.2
Reactions with Oxidising Agents
351
18.3
Reactions with Nucleophilic Reagents
352
18.4
Metallation and Reactions of C-Metallated
Furans
352
18.4.1
Direct Ring
C
-Н
Metallation
352
18.4.2
Metal-Halogen Exchange
353
18.5
Reactions with Radicals
353
18.6
Reactions with Reducing Agents
353
18.7
Electrocyclic Reactions (Ground State)
353
18.8
Reactions with Carbenes and Carbenoids
356
18.9
Photochemical Reactions
356
18.10
Furyl-C-X Compounds; Side-Chain Properties
356
18.11
Furan
Carboxylic Acids and Esters and Aldehydes
356
18.12
Oxy- and Amino-Furans
357
18.12.1
Oxy-Furans
357
18.12.2
Amino-Furans
358
18.13
Synthesis of
Furans
358
18.13.1
Ring Syntheses
359
18.13.2
Examples of Notable Syntheses of
Furans
363
Exercises
364
References
365
19
Typical Reactivity of
índoles, Benzo[¿]thiophenes,
Benzo[ft]furans, Isoindoles,
Benzole]thiophenes and Isobenzofurans
369
20
índoles:
Reactions and Synthesis
373
20.1
Reactions with Electrophilic Reagents
373
20.1.1
Substitution at Carbon
373
xii Contents
20.2
Reactions
with Oxidising Agents
20.3
Reactions
with Nucleophilic Reagents
20.4
Reactions
with Bases
20.4.1
Deprotonation of JV-Hydrogen and Reactions of Indolyl Anions
20.5
C-Metallation and Reactions of C-Metallated
índoles
20.5.1
Direct Ring
C
-Н
Metallation
20.5.2
Metal-Halogen Exchange
20.6
Reactions
with Radicals
20.7
Reactions
with Reducing Agents
20.8
Reactions
with Carbenes
20.9
Electrocyclic and Photochemical Reactions
20.10
Alkyl-Indoles
20.11
Reactions
of Indolyl-C-X Compounds
20.12
Indole Carboxylic
Acids
20.13
Oxy-Indoles
20.13.1
Oxindole
20.13.2
Indoxyl
20.13.3
Isatin
20.13.4
1-Hydroxyindole
20.14
Amino-Indoles
20.15
Aza-Indoles
20.15.1
Electrophilic Substitution
20.15.2
Nucleophilic Substitution
20.16
Synthesis
of
índoles
20.16.1
Ring Synthesis of
índoles
20.16.2
Ring Synthesis of Oxindoles
20.16.3
Ring Synthesis of Indoxyls
20.16.4
Ring Synthesis of Isatins
20.16.5
Synthesis of 1-Hydroxy-Indoles
20.16.6
Examples of Notable
Indole
Syntheses
20.16.7
Synthesis of Aza-Indoles
Exercises
References
385
386
386
386
388
388
390
391
392
392
393
394
395
396
397
397
398
399
399
400
400
401
401
402
402
416
417
418
418
418
421
422
423
21
Benzo[¿]thiophenes
and
Benzo[¿]furans:
Reactions and Synthesis
433
21.1
Reactions with Electrophilic Reagents
433
21.1.1
Substitution at Carbon
433
21.1.2
Addition to Sulfur in Benzothiophenes
434
21.2
Reactions with Nucleophilic Reagents
435
21.3
Metallation and Reactions of C-Metallated Benzothiophenes and Benzofiirans
435
21.4
Reactions with Radicals
436
21.5
Reactions with Oxidising and Reducing Agents
436
21.6
Electrocyclic Reactions
436
21.7
Oxy- and Amino-Benzothiophenes and -Benzofurans
437
21.8
Synthesis of Benzothiophenes and Benzofiirans
437
21.8.1
Ring Synthesis
437
Exercises
443
References
443
Contents xiii
22 Isoindoles, Benzolcjthiophenes and Isobenzof
urans:
Reactions and Synthesis
447
22.1
Reactions with Electrophilic Reagents
447
22.2
Electrocyclic Reactions
448
22.3
Phthalocyanines
449
22.4
Synthesis of Isoindoles, Benzo[c]thiophenes and Isobenzofurans
449
22.4.1
Isoindoles
449
22.4.2
Benzo[c]thiophenes
450
22.4.3
Isobenzofurans
451
Exercises
452
References
452
23
Typical Reactivity of
1,3-
and 1,2-AzoIes and
Вепго-ІЗ-
and -l^-Azoles
455
24
1,3-Azoles: Imidazoles, Thiazoles and Oxazoles: Reactions and Synthesis
461
24.1
Reactions with Electrophilic Reagents
461
24.1.1
Addition at Nitrogen
461
24.1.2
Substitution at Carbon
464
24.2
Reactions with Oxidising Agents
466
24.3
Reactions with Nucleophilic Reagents
466
24.3.1
With Replacement of Hydrogen
466
24.3.2
With Replacement of Halogen
466
24.4
Reactions with Bases
467
24.4.1
Deprotonation of Imidazole N-Hydrogen and Reactions of
Imidazolyl Anions
467
24.5
C-Metallation and Reactions of C-Metallated 1,3-Azoles
467
24.5.1
Direct Ring
C
-Н
Metallation
467
24.5.2
Metal-Halogen Exchange
468
24.6
Reactions with Radicals
468
24.7
Reactions with Reducing Agents
469
24.8
Electrocyclic Reactions
469
24.9
Alkyl-
1,3-Azoles
470
24.10
Quaternary 1,3-Azolium Salts
470
24.11
Oxy- and
Amino-
1,3-
Azoles
471
24.12
1,3-AzoleW-Oxides
473
24.13
Synthesis of 1,3-Azoles
473
24.13.1
Ring Synthesis
473
24.13.2
Examples of Notable Syntheses Involving 1,3-Azoles
478
Exercises
479
References
480
25
1,2-Azoles: Pyrazoles, Isothiazoles, Isoxazoles: Reactions and Synthesis
485
25.1
Reactions with Electrophilic Reagents
486
25.1.1
Addition at Nitrogen
486
25.1.2
Substitution at Carbon
487
25.2
Reactions with Oxidising Agents
488
25.3
Reactions with Nucleophilic Reagents
488
25.4
Reactions with Bases
488
25.4.1
Deprotonation of Pyrazole N-Hydrogen and Reactions of
Pyrazolyl Anions
488
xiv Contents
25.5 C-Metallation
and Reactions of
C-Metallated l^-Azoles
25.5.1
Direct
Ring
C
-Н
Metallation
25.5.2 Metal-Halogen Exchange
25.6
Reactions with Radicals
25.7
Reactions with Reducing Agents
25.8
Electrocyclic and Photochemical Reactions
25.9
Alkyl-
1,2-Azoles
25.10
Quaternary
1,2-
Azolium Salts
25.11
Oxy- and
Amino-
1
,2-azoles
25.12
Synthesis of
1,2-
Azoles
25.12.1
Ring Synthesis
Exercises
References
26
Benzanellated Azoles: Reactions and Synthesis
26.1
Reactions with Electrophilic Reagents
26.1.1
Addition at Nitrogen
26.1.2
Substitution at Carbon
26.2
Reactions with Nucleophilic Reagents
26.3
Reactions with Bases
26.3.1
Deprotonation of TV-Hydrogen and Reactions of Benzimidazolyl
and Indazolyl Anions
505
26.4
Ring Metallation and Reactions of C-Metallated Derivatives
505
26.5
Reactions with Reducing Agents
506
26.6
Electrocyclic Reactions
506
26.7
Quaternary Salts
506
26.8
Oxy- and Amino-Benzo-
1,3-
Azoles
507
26.9
Synthesis
507
26.9.1
Ring Synthesis of
Benzo-
1
,3-Azoles
507
26.9.2
Ring Synthesis of
Benzo-
1,2-
Azoles
509
References
512
27 Purines:
Reactions and Synthesis
515
27.1
Reactions with Electrophilic Reagents
516
27.1.1
Addition at Nitrogen
516
27.1.2
Substitution at Carbon
519
27.2
Reactions with Radicals
521
27.3
Reactions with Oxidising Agents
521
27.4
Reactions with Reducing Agents
521
27.5
Reactions with Nucleophilic Reagents
521
27.6
Reactions with Bases
524
27.6.1
Deprotonation of /V-Hydrogen and Reactions of Purinyl Anions
524
27.7
C-Metallation and Reactions of
C-Metallated Purines 524
27.7.1
Direct Ring
C
-Н
Metallation
524
27.7.2
Metal-Halogen Exchange
525
27.8
Oxy- and Amino-Purines
525
27.8.1
Oxy-Purines 52b
27.8.2
Amino-Purines
527
27.8.3
Thio-Purines
529
Contents xv
27.9 Alkyl-Purines 530
27.10 Purine Carboxylic
Acids
530
27.11
Synthesis of
Purines 530
27.11.1
Ring Synthesis
530
Π
.W.I Examples of Notable Syntheses Involving
Purines 534
Exercises
535
References
536
28
Heterocycles Containing a Ring-Junction Nitrogen (Bridgehead Compounds)
539
28.1
Indolizines
539
28.1.1
Reactions of Indolizines
540
28.1.2
Ring Synthesis of Indolizines
541
28.2
Aza-Indolizines
543
28.2.1
Imidazo[l,2-a]pyridines
543
28.2.2
Imidazo[l,5-a]pyridines
545
28.2.3
Pyrazolon^-ajpyridines
546
28.2.4
Triazolo- and Tetrazolo-Pyridines
547
28.2.5
Compounds with an Additional Nitrogen in the Six-Membered Ring
549
28.3
Quinolizinium and Related Systems
551
28.4
Pyrrolizine and Related Systems
551
28.5
Cyclazines
552
Exercises
553
References
553
29
Heterocycles Containing More Than Two
Heteroatoms
557
29.1
Five-Membered Rings
557
29.1.1
Azoles
557
29.1.2
Oxadiazoles and Thiadiazoles
569
29.1.3
Other Systems
574
29.2
Six-Membered Rings
574
29.2.1
Azines
574
29.3
Benzotriazoles
579
Exercises
581
References
581
30
Saturated and Partially Unsaturated Heterocyclic Compounds: Reactions and Synthesis
587
30.1
Five-and Six-Membered Rings
588
30.1.1
Pyrrolidines and Piperidines
588
30.1.2
Piperideines and Pyrrolines
589
30.1.3
Pyrans and Reduced
Furans
590
30.2
Three-Membered Rings
592
30.2.1
Three-Membered Rings with One
Heteroatom
592
30.2.2
Three-Membered Rings with Two
Heteroatoms
596
30.3
Four-Membered Rings
597
30.4
Metallation
598
30.5
Ring synthesis
599
30.5.1
Aziridines and Azirines
600
30.5.2
Azetidines and
ß-Lactams 602
30.5.3
Pyrrolidines
602
xvi
Contents
30.5.4
Piperidines
30.5.5
Saturated Oxygen Heterocycles
30.5.6
Saturated Sulfur Heterocycles
References
31
Special
Topics
603
604
605
606
609
31.1
Synthesis of Ring-Fluorinated Heterocycles
609
31.1.1
Electrophilic Fluorination
609
31.1.2
The Balz-Schiemann Reaction 611
31.1.3
Halogen Exchange (Halex) Reactions 612
31.1.4
Ring Synthesis Incorporating
Fluorinated
Starting Materials
612
31.2
Isotopically Labelled Heterocycles
616
31.2.1
Hazards Due to Radionuclides
616
31.2.2
Synthesis
616
31.2.3
PET (Positron Emission Tomography) 6
1
7
31.3
Bioprocesses in Heterocyclic Chemistry
619
31.4
Green Chemistry
620
31.5
Ionic Liquids 620
31.6
Applications and Occurrences of Heterocycles
621
31.6.1
Toxicity
622
31.6.2
Plastics and Polymers
622
31.6.3
Fungicides and Herbicides
623
31.6.4
Dyes and Pigments
623
31.6.5
Fluorescence-Based Applications
624
31.6.6
Electronic Applications
625
References
626
32
Heterocycles in Biochemistry; Heterocyclic Natural Products
629
32.1
Heterocyclic
Amino
Acids and Related Substances
629
32.2
Enzyme Co-Factors; Heterocyclic Vitamins; Co-Enzymes
630
32.2.1
Niacin (Vitamin B3) and Nicotinamide
Adeninę
Dinucleotide
Phosphate (NADF)
631
32.2.2
Pyridoxine (Vitamin B6) and Pyridoxal Phosphate (PLP)
631
32.2.3
Riboflavin
(Vitamin B2)
632
32.2.4
Thiamin (Vitamin B,) and Thiamine
Pyrophosphate
632
32.3
Porphobilinogen and the Pigments of Life
633
32.4
Ribonucleic Acid
(RNA)
and Deoxyribonucleic Acid
(DNA);
Genetic
Information;
Purines
and Pyrimidines
635
32.5
Heterocyclic Natural Products
637
32.5.1
Alkaloids
637
32.5.2
Marine Heterocycles
639
32.5.3
Halogenated Heterocycles
639
32.5.4
Macrocycles
Containing Oxazoles and Thiazoles
640
32.5.5
Other Nitrogen-Containing Natural Products
640
32.5.6
Anthocyanins and Flavones
641
References
542
33
Heterocycles in Medicine
645
33.1
Mechanisms of Drug Actions
646
33.1.1
Mimicking or Opposing the Effects of Physiological Hormones or
Neurotransmitters
646
Contents
xvii
33.1.2
Interaction with Enzymes
646
33.1.3
Physical Binding with, or Chemically Modifying,
Natural Macromolecules
646
33.2
The
Neurotransmitters
647
33.3
Drug Discovery and Development
647
33.3.1
Stages in the Life of a Drug
647
33.3.2
Drug Discovery
649
33.3.3
Chemical Development
649
33.3.4
Good Manufacturing Practice (GMP)
650
33.4
Heterocyclic Drugs
650
33.4.1
Histamine
650
33.4.2
Acetylcholine (ACh)
652
33.4.3
5-Hydroxytryptamine (5-HT)
653
33.4.4
Adrenaline and
Noradrenaline
654
33.4.5
Other Significant Cardiovascular Drugs
654
33.4.6
Drags Affecting Blood Clotting
655
33.4.7
Other Enzyme Inhibitors
656
33.4.8
Enzyme Induction
658
33.5
Drugs Acting on the CNS
658
33.6
Anti-Infective Agents
659
33.6.1
Anti-Parasitic Drags
659
33.6.2
Anti-Bacterial Drags
660
33.6.3
Anti-Viral Drags
661
33.7
Anti-Cancer Drugs
661
33.8
Photochemotherapy
663
33.8.1
Psoralen plus
UVA (PUVA)
Treatment
663
33.8.2
Photodynamic Therapy
(PDT)
664
References
664
Index
665
Heterocyclic
Fifth Edition
emistry
John Joule is Emeritus Professor in the School of Chemistry, The University of Manchester, UK
Keith Mills spent
25
years in the Medicinal Chemistry and Development Chemistry departments
ut
GlaxoSmithKline,
Stevenage,
UK, and is now cm independent consultant.
This book has so closely matched the requirements of its readership over the years that it has become the first
choice for chemists worldwide.
Heterocyclic chemistry comprises at least half of all organic chemistry research worldwide. In particular, the vast
majority of organic work done in the pharmaceutical and agrochemical industries is heterocyclic chemistry.
The fifth edition of Heterocyclic Chemistry maintains the principal
obiective
of earlier editions
-
to teach the
fundamentals of heterocyclic reactivity and synthesis in a way that is understandable to second- and third-year
undergraduate chemistry students. The inclusion of more advanced and current material also makes the book
a valuable reference text for postgraduate taught courses, postgraduate researchers, and chemists at all levels
working with heterocyclic compounds in industry.
Fully updated and expanded to reflect important 21st century advances, the fifth edition of this classic text
includes the following innovations:
I Extensive use of colour to highlight changes in structure and bonding during reactions
Ш
Entirely new chapters on organometallic heterocyclic chemistry, heterocyclic natural products,
especially in biochemical processes, and heterocycles in medicine
■
New sections focusing on heterocyclic fluorine compounds, isotopically labeled heterocycles, and
solid-phase chemistry, microwave heating and Bow reactors in the heterocyclic context
Essential teaching material in the early chapters is followed by short chapters throughout the text which capture
the essence of heterocyclic reactivity in concise resumes suitable as introductions or summaries, for example for
examination preparation. Detailed, systematic discussions cover the reactivity and synthesis of all the important
heterocyclic systems.
Origina]
references and references to reviews are given throughout the text, vital tor
postgraduate teaching and for research scientists. Problems, divided into straightforward revision exercises,
and more challenging questions (with solutions available online), help the reader to understand and apply the
principles of heterocyclic reactivity and synthesis.
|
| any_adam_object | 1 |
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| dewey-ones | 547 - Organic chemistry |
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| dewey-sort | 3547 259 |
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| discipline | Chemie / Pharmazie Chemie |
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| format | Book |
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| id | DE-604.BV035859028 |
| illustrated | Illustrated |
| indexdate | 2024-07-09T22:06:19Z |
| institution | BVB |
| isbn | 9781405133005 9781405193658 |
| language | English |
| oai_aleph_id | oai:aleph.bib-bvb.de:BVB01-018716927 |
| oclc_num | 699211494 |
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| physical | XXVII, 689 S. graph. Darst. |
| publishDate | 2010 |
| publishDateSearch | 2010 |
| publishDateSort | 2010 |
| publisher | Wiley |
| record_format | marc |
| spelling | Joule, John A. Verfasser (DE-588)1031833455 aut Heterocyclic chemistry John A. Joule ; Keith Mills 5. ed., 1. publ. Chichester Wiley 2010 XXVII, 689 S. graph. Darst. txt rdacontent n rdamedia nc rdacarrier Hier auch später erschienene, unveränderte Nachdrucke Heterocyclic chemistry Heterocyclische Verbindungen (DE-588)4159726-6 gnd rswk-swf Heterocyclische Verbindungen (DE-588)4159726-6 s DE-604 Mills, Keith Verfasser (DE-588)172914167 aut Digitalisierung UB Bayreuth application/pdf http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=018716927&sequence=000003&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA Inhaltsverzeichnis Digitalisierung UB Bayreuth application/pdf http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=018716927&sequence=000004&line_number=0002&func_code=DB_RECORDS&service_type=MEDIA Klappentext |
| spellingShingle | Joule, John A. Mills, Keith Heterocyclic chemistry Heterocyclic chemistry Heterocyclische Verbindungen (DE-588)4159726-6 gnd |
| subject_GND | (DE-588)4159726-6 |
| title | Heterocyclic chemistry |
| title_auth | Heterocyclic chemistry |
| title_exact_search | Heterocyclic chemistry |
| title_full | Heterocyclic chemistry John A. Joule ; Keith Mills |
| title_fullStr | Heterocyclic chemistry John A. Joule ; Keith Mills |
| title_full_unstemmed | Heterocyclic chemistry John A. Joule ; Keith Mills |
| title_short | Heterocyclic chemistry |
| title_sort | heterocyclic chemistry |
| topic | Heterocyclic chemistry Heterocyclische Verbindungen (DE-588)4159726-6 gnd |
| topic_facet | Heterocyclic chemistry Heterocyclische Verbindungen |
| url | http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=018716927&sequence=000003&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=018716927&sequence=000004&line_number=0002&func_code=DB_RECORDS&service_type=MEDIA |
| work_keys_str_mv | AT joulejohna heterocyclicchemistry AT millskeith heterocyclicchemistry |