Franklin

Heterocyclic chemistry / John A. Joule, Keith Mills.

Author/Creator:
Joule, J. A. (John Arthur)
Edition:
5th ed.
Publication:
Chichester, U.K. : Wiley, 2010.
Format/Description:
Book
1 online resource (xxviii, 689 pages) : illustrations
Subjects:
Heterocyclic chemistry.
System Details:
data file
Contents:
Heterocyclic Chemistry, Fifth Edition; Contents; Preface to the Fifth Edition; P.1 Hazards; P.2 How to Use This Textbook; Acknowledgements; References; Web Site; Biography; Definitions of Abbreviations; 1: Heterocyclic Nomenclature; 2: Structures and Spectroscopic Properties of Aromatic Heterocycles; 2.1 Carbocyclic Aromatic Systems; 2.1.1 Structures of Benzene and Naphthalene; 2.1.2 Aromatic Resonance Energy; 2.2 Structure of Six-Membered Heteroaromatic Systems; 2.2.1 Structure of Pyridine; 2.2.2 Structure of Diazines; 2.2.3 Structure of Pyridinium and Related Cations.
2.2.4 Structures of Pyridones and Pyrones2.3 Structure of Five-Membered Heteroaromatic Systems; 2.3.1 Structure of Pyrrole; 2.3.2 Structures of Thiophene and Furan; 2.3.3 Structures of Azoles; 2.3.4 Structures of Pyrryl and Related Anions; 2.4 Structures of Bicyclic Heteroaromatic Compounds; 2.5 Tautomerism in Heterocyclic Systems; 2.6 Mesoionic Systems; 2.7 Some Spectroscopic Properties of Some Heteroaromatic Systems; 2.7.1 Ultraviolet/Visible (Electronic) Spectroscopy; 2.7.2 Nuclear Magnetic Resonance (NMR) Spectroscopy; References; 3: Substitutions of Aromatic Heterocycles.
3.1 Electrophilic Addition at Nitrogen3.2 Electrophilic Substitution at Carbon; 3.2.1 Aromatic Electrophilic Substitution: Mechanism; 3.2.2 Six-Membered Heterocycles; 3.2.3 Five-Membered Heterocycles; 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-Hydrogen.
3.6 Oxidation and Reduction of Heterocyclic Rings3.7 ortho-Quinodimethanes in Heterocyclic Compound Synthesis; References; 4: Organometallic Heterocyclic Chemistry; 4.1 Preparation and Reactions of Organometallic Compounds; 4.1.1 Lithium; 4.1.2 Magnesium; 4.1.3 Zinc; 4.1.4 Copper; 4.1.5 Boron; 4.1.6 Silicon and Tin; 4.1.7 Mercury; 4.1.8 Palladium; 4.1.9 Side-Chain Metallation ('Lateral Metallation'); 4.2 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) Partner4.2.6 Other Nucleophiles; 4.2.7 The Ring Systems in Cross-Coupling Reactions; 4.2.8 Organometallic Selectivity; 4.2.9 Direct C-H Arylation; 4.2.10 N-Arylation; 4.2.11 Heck Reactions; 4.2.12 Carbonylation Reactions; References; 5: Methods in Heterocyclic Chemistry; 5.1 Solid-Phase Reactions and Related Methods; 5.1.1 Solid-Phase Reactions; 5.1.2 Solid-Supported Reagents and Scavengers; 5.1.3 Solid-Phase Extraction (SPE); 5.1.4 Soluble Polymer-Supported Reactions; 5.1.5 Phase Tags; 5.2 Microwave Heating; 5.3 Flow Reactors; 5.4 Hazards: Explosions.
Contents note continued: 28.2.2. Imidazo[1, 5-a]pyridines
28.2.3. Pyrazolo[1, 5-a]pyridines
28.2.4. Triazolo- and Tetrazolo-Pyridines
28.2.5. Compounds with an Additional Nitrogen in the Six-Membered Ring
28.3. Quinolizinium and Related Systems
28.4. Pyrrolizine and Related Systems
28.5. Cyclazines
Exercises
References
29. Heterocycles Containing More Than Two Heteroatoms
29.1. Five-Membered Rings
29.1.1. Azoles
29.1.2. Oxadiazoles and Thiadiazoles
29.1.3. Other Systems
29.2. Six-Membered Rings
29.2.1. Azines
29.3. Benzotriazoles
Exercises
References
30. Saturated and Partially Unsaturated Heterocyclic Compounds: Reactions and Synthesis
30.1. Five-and Six-Membered Rings
30.1.1. Pyrrolidines and Piperidines
30.1.2. Piperideines and Pyrrolines
30.1.3. Pyrans and Reduced Furans
30.2. Three-Membered Rings
30.2.1. Three-Membered Rings with One Heteroatom
30.2.2. Three-Membered Rings with Two Heteroatoms
30.3. Four-Membered Rings
30.4. Metallation
30.5. Ring synthesis
30.5.1. Aziridines and Azirines
30.5.2. Azetidines and β-Lactams
30.5.3. Pyrrolidines
30.5.4. Piperidines
30.5.5. Saturated Oxygen Heterocycles
30.5.6. Saturated Sulfur Heterocycles
References
31. Special Topics
31.1. Synthesis of Ring-Fluorinated Heterocycles
31.1.1. Electrophilic Fluorination
31.1.2. Balz-Schiemann Reaction
31.1.3. Halogen Exchange (Halex) Reactions
31.1.4. Ring Synthesis Incorporating Fluorinated Starting Materials
31.2. Isotopically labelled Heterocycles
31.2.1. Hazards Due to Radionuclides
31.2.2. Synthesis
31.2.3. PET (Positron Emission Tomography)
31.3. Bioprocesses in Heterocyclic Chemistry
31.4. Green Chemistry
31.5. Ionic liquids
31.6. Applications and Occurrences of Heterocycles
31.6.1. Toxicity
31.6.2. Plastics and Polymers
31.6.3. Fungicides and Herbicides
31.6.4. Dyes and Pigments
31.6.5. Fluorescence-Based Applications
31.6.6. Electronic Applications
References
32. Heterocycles in Biochemistry; Heterocyclic Natural Products
32.1. Heterocyclic Amino Acids and Related Substances
32.2. Enzyme Co-Factors; Heterocyclic Vitamins; Co-Enzymes
32.2.1. Niacin (Vitamin B3) and Nicotinamide Adenine Dinucleotide Phosphate (NADP+)
32.2.2. Pyridoxine (Vitamin B6) and Pyridoxal Phosphate (PLP)
32.2.3. Riboflavin (Vitamin B2)
32.2.4. Thiamin (Vitamin B1) and Thiamine Pyrophosphate
32.3. Porphobilinogen and the ̀Pigments of Life'
32.4. Ribonucleic Acid (RNA) and Deoxyribonucleic Acid (DNA); Genetic Information; Purines and Pyrimidines
32.5. Heterocyclic Natural Products
32.5.1. Alkaloids
32.5.2. Marine Heterocycles
32.5.3. Halogenated Heterocycles
32.5.4. Macrocycles Containing Oxazoles and Thiazoles
32.5.5. Other Nitrogen-Containing Natural Products
32.5.6. Anthocyanins and Flavones
References
33. Heterocycles in Medicine
33.1. Mechanisms of Drug Actions
33.1.1. Mimicking or Opposing the Effects of Physiological Hormones or Neurotransmitters
33.1.2. Interaction with Enzymes
33.1.3. Physical Binding with, or Chemically Modifying, Natural Macromolecules
33.2. Neurotransmitters
33.3. Drug Discovery and Development
33.3.1. Stages in the life of a Drug
33.3.2. Drug Discovery
33.3.3. Chemical Development
33.3.4. Good Manufacturing Practice (GMP)
33.4. Heterocyclic Drugs
33.4.1. Histamine
33.4.2. Acetylcholine (ACh)
33.4.3. 5-Hydroxytryptamine (5-HT)
33.4.4. Adrenaline and Noradrenaline
33.4.5. Other Significant Cardiovascular Drugs
33.4.6. Drugs Affecting Blood Clotting
33.4.7. Other Enzyme Inhibitors
33.4.8. Enzyme Induction
33.5. Drugs Acting on the CNS
33.6. Anti-Infective Agents
33.6.1. Anti-Parasitic Drugs
33.6.2. Anti-Bacterial Drugs
33.6.3. Anti-Viral Drugs
33.7. Anti-Cancer Drugs
33.8. Photochemotherapy
33.8.1. Psoralen plus UVA (PUVA) Treatment
33.8.2. Photodynamic Therapy (PDT)
References.
Machine generated contents note: 1. Heterocyclic Nomenclature
2. Structures and Spectroscopic Properties of Aromatic Heterocycles
2.1. Carbocyclic Aromatic Systems
2.1.1. Structures of Benzene and Naphthalene
2.1.2. Aromatic Resonance Energy
2.2. Structure of Six-Membered Heteroaromatic Systems
2.2.1. Structure of Pyridine
2.2.2. Structure of Diazines
2.2.3. Structures of Pyridinium and Related Cations
2.2.4. Structures of Pyridones and Pyrones
2.3. Structure of Five-Membered Heteroaromatic Systems
2.3.1. Structure of Pyrrole
2.3.2. Structures of Thiophene and Furan
2.3.3. Structures of Azoles
2.3.4. Structures of Pyrrole and Related Anions
2.4. Structures of Bicyclic Heteroaromatic Compounds
2.5. Tautomerism in Heterocyclic Systems
2.6. Mesoionic Systems
2.7. Some Spectroscopic Properties of Some Heteroaromatic Systems
2.7.1. Ultraviolet/Visible (Electronic) Spectroscopy
2.7.2. Nuclear Magnetic Resonance (NMR) Spectroscopy
References
3. Substitutions of Aromatic Heterocycles
3.1. Electrophilic Addition at Nitrogen
3.2. Electrophilic Substitution at Carbon
3.2.1. Aromatic Electrophilic Substitution: Mechanism
3.2.2. Six-Membered Heterocycles
3.2.3. Five-Membered Heterocycles
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-Hydrogen
3.6. Oxidation and Reduction of Heterocyclic Rings
3.7. ort/zo-Quinodimethanes in Heterocyclic Compound Synthesis
References
4. Organometallic Heterocyclic Chemistry
4.1. Preparation and Reactions of Organometallic Compounds
4.1.1. Lithium
4.1.2. Magnesium
4.1.3. Zinc
4.1.4. Copper
4.1.5. Boron
4.1.6. Silicon and Tin
4.1.7. Mercury
4.1.8. Palladium
4.1.9. Side-Chain Metallation ('Lateral Metallation')
4.2. Transition Metal-Catalysed Reactions
4.2.1. Basic Palladium Processes
4.2.2. Catalysts
4.2.3. Electrophilic Partner; The Halides/Leaving Groups
4.2.4. Cross-Coupling Reactions
4.2.5. Nucleophilic (Organometallic) Partner
4.2.6. Other Nucleophiles
4.2.7. Ring Systems in Cross-Coupling Reactions
4.2.8. Organometallic Selectivity
4.2.9. Direct C-H Arylation
4.2.10. N- Arylation
4.2.11. Heck Reactions
4.2.12. Carbonylation Reactions
References
5. Methods in Heterocyclic Chemistry
5.1. Solid-Phase Reactions and Related Methods
5.1.1. Solid-Phase Reactions
5.1.2. Solid-Supported Reagents and Scavengers
5.1.3. Solid-Phase Extraction (SPE)
5.1.4. Soluble Polymer-Supported Reactions
5.1.5. Phase Tags
5.2. Microwave Heating
5.3. Flow Reactors
5.4. Hazards: Explosions
References
6. Ring Synthesis of Aromatic Heterocycles
6.1. Reaction Types Most Frequently Used in Heterocyclic Ring Synthesis
6.2. Typical Reactant Combinations
6.2.1. Typical Ring Synthesis of a Pyrrole Involving Only C-Heteroatom Bond Formation
6.2.2. Typical Ring Synthesis of a Pyridine Involving Only C-Heteroatom Bond Formation
6.2.3. Typical Ring Syntheses Involving C-Heteroatom C-C Bond Formations
6.3. Summary
6.4. Electrocyclic Processes in Heterocyclic Ring Synthesis
6.5. Nitrenes in Heterocyclic Ring Synthesis
6.6. Palladium Catalysis in the Synthesis of Benzo-Fused Heterocycles
References
7. Typical Reactivity of Pyridines, Quinolines and Isoquinolines
8. Pyridines: Reactions and Synthesis
8.1. Reactions with Electrophilic Reagents
8.1.1. Addition to Nitrogen
8.1.2. Substitution at Carbon
8.2. Reactions with Oxidising Agents
8.3. Reactions with Nucleophilic Reagents
8.3.1. Nucleophilic Substitution with ̀Hydride' Transfer
8.3.2. Nucleophilic Substitution with Displacement of Good Leaving Groups
8.4. Metallation and Reactions of C-Metallated-Pyridines
8.4.1. Direct Ring C-H Metallation
8.4.2. Metal-Halogen Exchange
8.5. Reactions with Radicals; Reactions of Pyridyl Radicals
8.5.1. Halogenation
8.5.2. Carbon Radicals
8.5.3. Dimerisation
8.5.4. Pyridinyl Radicals
8.6. Reactions with Reducing Agents
8.7. Electrocyclic Reactions (Ground State)
8.8. Photochemical Reactions
8.9. Oxy-and Amino-Pyridines
8.9.1. Structure
8.9.2. Reactions of Pyridones
8.9.3. Reactions of Amino-Pyridines
8.10. Alkyl-Pyridines
8.11. Pyridine Aldehydes, Ketones, Carboxylic Acids and Esters
8.12. Quaternary Pyridinium Salts
8.12.1. Reduction and Oxidation
8.12.2. Organometallic and Other Nucleophilic Additions
8.12.3. Nucleophilic Addition Followed by Ring Opening
8.12.4. Cyclisations Involving an α-Position or an α-Substituent
8.12.5. N-Dealkylation
8.13. Pyridine N-oxides
8.13.1. Electrophilic Addition and Substitution
8.13.2. Nucleophilic Addition and Substitution
8.13.3. Addition of Nucleophiles then Loss of Oxide
8.14. Synthesis of Pyridines
8.14.1. Ring Synthesis
8.14.2. Examples of Notable Syntheses of Pyridine Compounds
Exercises
References
9. Quinolines and Isoquinolines: Reactions and Synthesis
9.1. Reactions with Electrophilic Reagents
9.1.1. Addition to Nitrogen
9.1.2. Substitution at Carbon
9.2. Reactions with Oxidising Agents
9.3. Reactions with Nucleophilic Reagents
9.3.1. Nucleophilic Substitution with ̀Hydride' Transfer
9.3.2. Nucleophilic Substitution with Displacement of Good Leaving Groups
9.4. Metallation and Reactions of C-Metallated Quinolines and Isoquinolines
9.4.1. Direct Ring C-H Metallation
9.4.2. Metal-Halogen Exchange
9.5. Reactions with Radicals
9.6. Reactions with Reducing Agents
9.7. Electrocyclic Reactions (Ground State)
9.8. Photochemical Reactions
9.9. Oxy-Quinolines and Oxy-Isoquinolines
9.10. Amino-Quinolines and Amino-Isoquinolines
9.11. Alkyl-Quinolines and Alkyl-Isoquinolines
9.12. Quinoline and Isoquinoline Carboxylic Acids and Esters
9.13. Quaternary Quinolinium and Isoquinolinium Salts
9.14. Quinoline and Isoquinoline N-Oxides
9.15. Synthesis of Quinolines and Isoquinolines
9.15.1. Ring Syntheses
9.15.2. Examples of Notable Syntheses of Quinoline and Isoquinoline Compounds
Exercises
References
10. Typical Reactivity of Pyrylium and Benzopyrylium Ions, Pyrones and Benzopyrones
11. Pyryliums, 2- and 4-Pyrones: Reactions and Synthesis
11.1. Reactions of Pyrylium Cations
11.1.1. Reactions with Electrophilic Reagents
11.1.2. Addition Reactions with Nucleophilic Reagents
11.1.3. Substitution Reactions with Nucleophilic Reagents
11.1.4. Reactions with Radicals
11.1.5. Reactions with Reducing Agents
11.1.6. Photochemical Reactions
11.1.7. Reactions with Dipolarophiles; Cycloadditions
11.1.8. Alkyl-Pyryliums
11.2. 2-Pyrones and 4-Pyrones (2H-Pyran-2-ones and 4H-Pyran-4-ones; α- and γ-Pyrones)
11.2.1. Structure of Pyrones
11.2.2. Reactions of Pyrones
11.3. Synthesis of Pyryliums
11.3.1. From 1, 5-Dicarbonyl Compounds
11.3.2. Alkene Acylation
11.3.3. From 1, 3-Dicarbonyl Compounds and Ketones
11.4. Synthesis of 2-Pyrones
11.4.1. From 1, 3-Keto(aldehydo)-Acids and Carbonyl Compounds
11.4.2. Other Methods
11.5. Synthesis of 4-Pyrones
Exercises
References
12. Benzopyryliums and Benzopyrones: Reactions and Synthesis
12.1. Reactions of Benzopyryliums
12.1.1. Reactions with Electrophilic Reagents
12.1.2. Reactions with Oxidising Agents
12.1.3. Reactions with Nucleophilic Reagents
12.1.4. Reactions with Reducing Agents
12.1.5. Alky l-Benzopyryliums
12.2. Benzopyrones (Chromones, Coumarins and Isocoumarins)
12.2.1. Reactions with Electrophilic Reagents
12.2.2. Reactions with Oxidising Agents
12.2.3. Reactions with Nucleophilic Reagents
12.3. Synthesis of Benzopyryliums, Chromones, Coumarins and Isocoumarins
12.3.1. Ring Synthesis of 1-Benzopyryliums
12.3.2. Ring Synthesis of Coumarins
12.3.3. Ring Synthesis of Chromones
12.3.4. Ring Synthesis of 2-Benzopyryhums
12.3.5. Ring Synthesis of Isocoumarins
12.3.6. Notable Examples of Benzopyrylium and Benzopyrone Syntheses
Exercises
References
13. Typical Reactivity of the Diazine: Pyridazine, Pyrimidine and Pyrazine
14. Diazine: Pyridazine, Pyrimidine and Pyrazine: Reactions and Synthesis
14.1. Reactions with Electrophilic Reagents
14.1.1. Addition at Nitrogen
14.1.2. Substitution at Carbon
14.2. Reactions with Oxidising Agents
14.3. Reactions with Nucleophilic Reagents
14.3.1. Nucleophilic Substitution with ̀Hydride' Transfer
14.3.2. Nucleophilic Substitution with Displacement of Good Leaving Groups
14.4. Metallation and Reactions of C-Metallated Diazines
14.4.1. Direct Ring C-H Metallation
14.4.2. Metal-Halogen Exchange
14.5. Reactions with Reducing Agents
14.6. Reactions with Radicals
14.7. Electrocyclic Reactions
14.8. Diazine N-Oxides
14.9. Oxy-Diazines
14.9.1. Structure of Oxy-Diazines
14.9.2. Reactions of Oxy-Diazines
14.10. Amino-Diazines
14.11. Alkyl-Diazines.
Notes:
Includes bibliographical references and index.
Electronic reproduction. Ann Arbor, MI Available via World Wide Web.
Print version record.
Contributor:
Mills, K. (Keith)
ProQuest ebook central
Other format:
Print version: Joule, J.A. (John Arthur). Heterocyclic chemistry.
ISBN:
9781615833887
1615833889
9780470685976
0470685972
9781405193658
9781405133005
9786612549380
6612549386
1405193654
1405133007
Publisher Number:
99984506576
9786612549380
Access Restriction:
Restricted for use by site license.
Loading...
Location Notes Your Loan Policy
Description Status Barcode Your Loan Policy