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Summary:

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 objective 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. --
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. Original references and references to reviews are given throughout the text, vital for 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. --Book Jacket.

Table of Contents:

• 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
• Contents note continued: 14.11. Alkyl-Diazines
• 14.12. Quaternary Diazinium Salts
• 14.13. Synthesis of Diazines
• 14.13.1. Pyridazines
• 14.13.2. Pyrimidines
• 14.13.3. Pyrazines
• 14.13.4. Notable Syntheses of Diazines
• 14.14. Pteridines
• Exercises
• References
• 15. Typical Reactivity of Pyrroles, Furans and Thiophenes
• 16. Pyrroles: Reactions and Synthesis
• 16.1. Reactions with Electrophilic Reagents
• 16.1.1. Substitution at Carbon
• 16.2. Reactions with Oxidising Agents
• 16.3. Reactions with Nucleophilic Reagents
• 16.4. Reactions with Bases
• 16.4.1. Deprotonation of N-Hydrogen and Reactions of Pyrryl Anions
• 16.4.2. Lithium, Sodium, Potassium and Magnesium Derivatives
• 16.5. C-Metallation and Reactions of C-Metallated Pyrroles
• 16.5.1. Direct Ring C-H Metallation
• 16.5.2. Metal-Halogen Exchange
• 16.6. Reactions with Radicals
• 16.7. Reactions with Reducing Agents
• 16.8. Electrocyclic Reactions (Ground State)
• 16.9. Reactions with Carbenes and Carbenoids
• 16.10. Photochemical Reactions
• 16.11. Pyrryl-C-X Compounds
• 16.12. Pyrrole Aldehydes and Ketones
• 16.13. Pyrrole Carboxylic Acids
• 16.14. Pyrrole Carboxylic Acid Esters
• 16.15. Oxy- and Amino-Pyrroles
• 16.15.1. 2-Oxy-Pyrroles
• 16.15.2. 3-Oxy-Pyrroles
• 16.15.3. Amino-Pyrroles
• 16.16. Synthesis of Pyrroles
• 16.16.1. Ring Synthesis
• 16.16.2. Some Notable Syntheses of Pyrroles
• Exercises
• References
• 17. Thiophenes: Reactions and Synthesis
• 17.1. Reactions with Electrophilic Reagents
• 17.1.1. Substitution at Carbon
• 17.1.2. Addition at Sulfur
• 17.2. Reactions with Oxidising Agents
• 17.3. Reactions with Nucleophilic Reagents
• 17.4. Metallation and Reactions of C-Metallated Thiophenes
• 17.4.1. Direct Ring C-H Metallation
• 17.4.2. Metal-Halogen Exchange
• 17.5. Reactions with Radicals
• 17.6. Reactions with Reducing Agents
• 17.7. Electrocyclic Reactions (Ground State)
• 17.8. Photochemical Reactions
• 17.9. Thiophene-C-X Compounds: Thenyl Derivatives
• 17.10. Thiophene Aldehydes and Ketones, and Carboxylic Acids and Esters
• 17.11. Oxy-and Amino-Thiophenes
• 17.11.1. Oxy-Thiophenes
• 17.11.2. Amino-Thiophenes
• 17.12. Synthesis of Thiophenes
• 17.12.1. Ring Synthesis
• 17.12.2. Examples of Notable Syntheses of Thiophene Compounds
• Exercises
• References
• 18. Furans: Reactions and Synthesis
• 18.1. Reactions with Electrophilic Reagents
• 18.1.1. Substitution at Carbon
• 18.2. Reactions with Oxidising Agents
• 18.3. Reactions with Nucleophilic Reagents
• 18.4. Metallation and Reactions of C-Metallated Furans
• 18.4.1. Direct Ring C-H Metallation
• 18.4.2. Metal-Halogen Exchange
• 18.5. Reactions with Radicals
• 18.6. Reactions with Reducing Agents
• 18.7. Electrocyclic Reactions (Ground State)
• 18.8. Reactions with Carbenes and Carbenoids
• 18.9. Photochemical Reactions
• 18.10. Fury1-C-X Compounds; Side-Chain Properties
• 18.11. Furan Carboxylic Acids and Esters and Aldehydes
• 18.12. Oxy-and Amino-Furans
• 18.12.1. Oxy-Furans
• 18.12.2. Amino-Furans
• 18.13. Synthesis of Furans
• 18.13.1. Ring Syntheses
• 18.13.2. Examples of Notable Syntheses of Furans
• Exercises
• References
• 19. Typical Reactivity of Indoles, Benzo[b]thiophenes, Benzo[b]furans, Isoindoles, Benzo[c]thiophenes and Isobenzofurans
• 20. Indoles: Reactions and Synthesis
• 20.1. Reactions with Electrophilic Reagents
• 20.1.1. Substitution at Carbon
• 20.2. Reactions with Oxidising Agents
• 20.3. Reactions with Nucleophilic Reagents
• 20.4. Reactions with Bases
• 20.4.1. Deprotonation of N-Hydrogen and Reactions of Indolyl Anions
• 20.5. C-Metallation and Reactions of C-Metallated Indoles
• 20.5.1. Direct Ring C-H 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. Inoxyl
• 20.13.3. Isatin
• 20.13.4. 1-Hydroxy indole
• 20.14. Amino-Indoles
• 20.15. Aza-Indoles
• 20.15.1. Electrophilic Substitution
• 20.15.2. Nucleophilic Substitution
• 20.16. Synthesis of Indoles
• 20.16.1. Ring Synthesis of Indoles
• 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
• 21. Benzo[b]thiophenes and Benzo[b]furans: Reactions and Synthesis
• 21.1. Reactions with Electrophilic Reagents
• 21.1.1. Substitution at Carbon
• 21.1.2. Addition to Sulfur in Benzothiophenes
• 21.2. Reactions with Nucleophilic Reagents
• 21.3. Metallation and Reactions of C-Metallated Benzothiophenes and Benzofurans
• 21.4. Reactions with Radicals
• 21.5. Reactions with Oxidising and Reducing Agents
• 21.6. Electrocyclic Reactions
• 21.7. Oxy-and Amino-Benzothiophenes and-Benzofurans
• 21.8. Synthesis of Benzothiophenes and Benzofurans
• 21.8.1. Ring Synthesis
• Exercises
• References
• 22. Isoindoles, Benzo[c]thiophenes and Isobenzofurans: Reactions and Synthesis
• 22.1. Reactions with Electrophilic Reagents
• 22.2. Electrocyclic Reactions
• 22.3. Phthalocyanines
• 22.4. Synthesis of Isoindoles, Benzo[c]thiophenes and Isobenzofurans
• 22.4.1. Isoindoles
• 22.4.2. Benzo[c]thiophenes
• 22.4.3. Isobenzofurans
• Exercises
• References
• 23. Typical Reactivity of 1, 3- and 1, 2-Azoles and Benzo-1, 3- and -1, 2-Azoles
• 24. 1, 3-Azoles: Imidazoles, Thiazoles and Oxazoles: Reactions and Synthesis
• 24.1. Reactions with Electrophilic Reagents
• 24.1.1. Addition at Nitrogen
• 24.1.2. Substitution at Carbon
• 24.2. Reactions with Oxidising Agents
• 24.3. Reactions with Nucleophilic Reagents
• 24.3.1. With Replacement of Hydrogen
• 24.3.2. With Replacement of Halogen
• 24.4. Reactions with Bases
• 24.4.1. Deprotonation of Imidazole N-Hydrogen and Reactions of Imidazolyl Anions
• 24.5. C-Metallation and Reactions of C-Metallated 1, 3-Azoles
• 24.5.1. Direct Ring C-H Metallation
• 24.5.2. Metal-Halogen Exchange
• 24.6. Reactions with Radicals
• 24.7. Reactions with Reducing Agents
• 24.8. Electrocyclic Reactions
• 24.9. Alkyl-1, 3-Azoles
• 24.10. Quaternary 1, 3-Azolium Salts
• 24.11. Oxy-and Amino-1, 3-Azoles
• 24.12. 1, 3-Azole N-Oxides
• 24.13. Synthesis of 1, 3-Azoles
• 24.13.1. Ring Synthesis
• 24.13.2. Examples of Notable Syntheses Involving 1, 3-Azoles
• Exercises
• References
• 25. 1, 2-Azoles: Pyrazoles, Isothiazoles, Isoxazoles: Reactions and Synthesis
• 25.1. Reactions with Electrophilic Reagents
• 25.1.1. Addition at Nitrogen
• 25.1.2. Substitution at Carbon
• 25.2. Reactions with Oxidising Agents
• 25.3. Reactions with Nucleophilic Reagents
• 25.4. Reactions with Bases
• 25.4.1. Deprotonation of Pyrazole N-Hydrogen and Reactions of Pyrazolyl Anions
• 25.5. C-Metallation and Reactions of C-Metallated 1, 2-Azoles
• 25.5.1. Direct Ring C-H 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 N-Hydrogen and Reactions of Benzimidazolyl and Indazolyl Anions
• 26.4. Ring Metallation and Reactions of
• C-Metallated Derivatives
• 26.5. Reactions with Reducing Agents
• 26.6. Electrocyclic Reactions
• 26.7. Quaternary Salts
• 26.8. Oxy-and Amino-Benzo-1, 3-Azoles
• 26.9. Synthesis
• 26.9.1. Ring Synthesis of Benzo-1, 3-Azoles
• 26.9.2. Ring Synthesis of Benzo-1, 2-Azoles
• References
• 27. Purines: Reactions and Synthesis
• 27.1. Reactions with Electrophilic Reagents
• 27.1.1. Addition at Nitrogen
• 27.1.2. Substitution at Carbon
• 27.2. Reactions with Radicals
• 27.3. Reactions with Oxidising Agents
• 27.4. Reactions with Reducing Agents
• 27.5. Reactions with Nucleophilic Reagents
• 27.6. Reactions with Bases
• 27.6.1. Deprotonation of N-Hydrogen and Reactions of Purinyl Anions
• 27.7. C-Metallation and Reactions of C-Metallated Purines
• 27.7.1. Direct Ring C-H Metallation
• 27.7.2. Metal-Halogen Exchange
• 27.8. Oxy- and Amino-Purines
• 27.8.1. Oxy-Purines
• 27.8.2. Amino-Purines
• 27.8.3. Thio-Purines
• 27.9. Alkyl-Purines
• 27.10. Purine Carboxylic Acids
• 27.11. Synthesis of Purines
• 27.11.1. Ring Synthesis
• 27.11.2. Examples of Notable Syntheses Involving Purines
• Exercises
• References
• 28. Heterocycles Containing a Ring-Junction Nitrogen (Bridgehead Compounds)
• 28.1. Indolizines
• 28.1.1. Reactions of Indolizines
• 28.1.2. Ring Synthesis of Indolizines
• 28.2. Aza-Indolizines
• Contents note continued: 28.2.1. Imidazo[1, 2-a]pyridines
• 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.

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Author/Creator:

Joule, J. A. (John Arthur)

Contributors:

Mills, K. (Keith)

Languages:

English

Language Notes:

Item content: English

Main Work:

Heterocyclic chemistry [by Joule, J.A.]

Other Related Resources:

Print version: Heterocyclic chemistry [by Joule, J.A.] (5th ed.; Chichester, U.K. : Wiley, 2010 — ISBN 9781405133005; LCCN 2009028759)

Subjects:

Heterocyclic chemistry

General Notes:

Includes bibliographical references and index.
Description based on print version record.
Electronic reproduction. Palo Alto, Calif. Available via World Wide Web.

Physical Description:

1 online resource.

Digital Characteristics:

text file

Call Numbers:

QD400 .J59 2010eb

ISBNs:

9780470685976 (electronic bk.)
0470685972 (electronic bk.)

OCLC Numbers:

643116330

Other Control Numbers:

EBC496060 (source: MiAaPQ)