Heterocyclic Chemistry by Joule, John A. -- Read -- Imperial Library of Trantor

Index

Contents Title Page Copyright Preface to the Fifth Edition Biography Definitions of Abbreviations 1 Heterocyclic Nomenclature 2 Structures and Spectroscopic Properties of Aromatic Heterocycles

2.1 Carbocyclic Aromatic Systems 2.2 Structure of Six-Membered Heteroaromatic Systems 2.3 Structure of Five-Membered Heteroaromatic Systems5 2.4 Structures of Bicyclic Heteroaromatic Compounds 2.5 Tautomerism in Heterocyclic Systems6,7 2.6 Mesoionic Systems8 2.7 Some Spectroscopic Properties of Some Heteroaromatic Systems References

3 Substitutions of Aromatic Heterocycles

3.1 Electrophilic Addition at Nitrogen 3.2 Electrophilic Substitution at Carbon6 3.3 Nucleophilic Substitution at Carbon33 3.4 Radical Substitution at Carbon45 3.5 Deprotonation of N-Hydrogen59 3.6 Oxidation and Reduction60 of Heterocyclic Rings 3.7 ortho-Quinodimethanes in Heterocyclic Compound Synthesis61 References

4 Organometallic Heterocyclic Chemistry

4.1 Preparation and Reactions of Organometallic Compounds 4.2 Transition Metal-Catalysed Reactions108 References

5 Methods in Heterocyclic Chemistry

5.1 Solid-Phase Reactions1 and Related Methods 5.2 Microwave Heating23 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 6.3 Summary 6.4 Electrocyclic Processes in Heterocyclic Ring Synthesis 6.5 Nitrenes in Heterocyclic Ring Synthesis8 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 8.2 Reactions with Oxidising Agents 8.3 Reactions with Nucleophilic Reagents 8.4 Metallation and Reactions of C-Metallated-Pyridines 8.5 Reactions with Radicals; Reactions of Pyridyl Radicals 8.6 Reactions with Reducing Agents 8.7 Electrocyclic Reactions (Ground State) 8.8 Photochemical Reactions 8.9 Oxy- and Amino-Pyridines 8.10 Alkyl-Pyridines 8.11 Pyridine Aldehydes, Ketones, Carboxylic Acids and Esters 8.12 Quaternary Pyridinium Salts 8.13 Pyridine N-oxides245 8.14 Synthesis of Pyridines Exercises References

9 Quinolines and Isoquinolines: Reactions and Synthesis

9.1 Reactions with Electrophilic Reagents 9.2 Reactions with Oxidising Agents 9.3 Reactions with Nucleophilic Reagents 9.4 Metallation and Reactions of C-Metallated Quinolines and Isoquinolines 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 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 Cations4,5 11.2 2-Pyrones and 4-Pyrones (2H-Pyran-2-ones and 4.H-Pyran-4-ones; α- and γ-Pyrones) 11.3 Synthesis of Pyryliums1,7a 11.4 Synthesis of 2-Pyrones 11.5 Synthesis of 4-Pyrones Exercises References

12 Benzopyryliums and Benzopyrones: Reactions and Synthesis

12.1 Reactions of Benzopyryliums 12.2 Benzopyrones (Chromones, Coumarins and Isocoumarins) 12.3 Synthesis of Benzopyryliums, Chromones, Coumarins and Isocoumarins Exercises References

13 Typical Reactivity of the Diazine: Pyridazine, Pyrimidine and Pyrazine 14 The Diazines: Pyridazine, Pyrimidine, and Pyrazine: Reactions and Synthesis

14.1 Reactions with Electrophilic Reagents 14.2 Reactions with Oxidising Agents 14.3 Reactions with Nucleophilic Reagents 14.4 Metallation and Reactions of C-Metallated Diazines50 14.5 Reactions with Reducing Agents 14.6 Reactions with Radicals 14.7 Electrocyclic Reactions 14.8 Diazine N-Oxides79 14.9 Oxy-Diazines 14.10 Amino-Diazines 14.11 Alkyl-Diazines 14.12 Quaternary Diazinium Salts 14.13 Synthesis 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 Reagents5 16.2 Reactions with Oxidising Agents65 16.3 Reactions with Nucleophilic Reagents 16.4 Reactions with Bases 16.5 C-Metallation and Reactions of C-Metallated Pyrroles 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 Reactions120 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 16.16 Synthesis of Pyrroles5,140 Exercises References

17 Thiophenes: Reactions and Synthesis

17.1 Reactions with Electrophilic Reagents 17.2 Reactions with Oxidising Agents 17.3 Reactions with Nucleophilic Reagents 17.4 Metallation and Reactions of C-Metallated Thiophenes 17.5 Reactions with Radicals 17.6 Reactions with Reducing Agents 17.7 Electrocyclic Reactions (Ground State)118 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 17.12 Synthesis of Thiophenes146 Exercises References

18 Furans: Reactions and Synthesis

18.1 Reactions with Electrophilic Reagents 18.2 Reactions with Oxidising Agents 18.3 Reactions with Nucleophilic Reagents 18.4 Metallation and Reactions of C-Metallated Furans 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 Furyl-C–X Compounds; Side-Chain Properties 18.11 Furan Carboxylic Acids and Esters and Aldehydes 18.12 Oxy- and Amino-Furans 18.13 Synthesis 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 20.2 Reactions with Oxidising Agents 20.3 Reactions with Nucleophilic Reagents (see also 20.13.4) 20.4 Reactions with Bases 20.5 C-Metallation and Reactions of C-Metallated Indoles 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 20.14 Amino-Indoles 20.15 Aza-Indoles273,274 20.16 Synthesis of Indoles282 Exercises References

21 Benzo[b]thiophenes and Benzo[b]furans: Reactions and Synthesis

21.1 Reactions with Electrophilic Reagents 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-58 and Amino-Benzothiophenes and -Benzofurans 21.8 Synthesis of Benzothiophenes and Benzofurans Exercises References

22 Isoindoles, Benzo[c]thiophenes and Isobenzofurans: Reactions and Synthesis

22.1 Reactions with Electrophilic Reagents 22.2 Electrocyclic Reactions 22.3 Phthalocyanines21 22.4 Synthesis of Isoindoles, Benzo[c]thiophenes and 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 24.2 Reactions with Oxidising Agents 24.3 Reactions with Nucleophilic Reagents 24.4 Reactions with Bases 24.5 C-Metallation and Reactions of C-Metallated 1,3-Azoles57 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-103,104 and Amino-1051,3-Azoles 24.12 1,3-Azole N-Oxides 24.13 Synthesis of 1,3-Azoles119,120,121 Exercises References

25 1,2-Azoles: Pyrazoles, Isothiazoles, Isoxazoles: Reactions and Synthesis

25.1 Reactions with Electrophilic Reagents 25.2 Reactions with Oxidising Agents 25.3 Reactions with Nucleophilic Reagents 25.4 Reactions with Bases 25.5 C-Metallation and Reactions of C-Metallated 1,2-Azoles42 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-Azoles98 Exercises References

26 Benzanellated Azoles: Reactions and Synthesis

26.1 Reactions with Electrophilic Reagents 26.2 Reactions with Nucleophilic Reagents 26.3 Reactions with Bases 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 References

27 Purines: Reactions and Synthesis

27.1 Reactions with Electrophilic Reagents 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 27.7 C-Metallation and Reactions of C-Metallated Purines 27.8 Oxy-and Amino-Purines 27.9 Alkyl-Purines 27.10 Purine Carboxylic Acids 27.11 Synthesis of Purines Exercises References

28 Heterocycles Containing a Ring-Junction Nitrogen (Bridgehead Compounds)

28.1 Indolizines2 28.2 Aza-Indolizines 28.3 Quinolizinium86 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 29.2 Six-Membered Rings 29.3 Benzotriazoles Exercises References

30 Saturated and Partially Unsaturated Heterocyclic Compounds: Reactions and Synthesis

30.1 Five- and Six-Membered Rings 30.2 Three-Membered Rings 30.3 Four-Membered Rings 30.4 Metallation 30.5 Ring Synthesis References

31 Special Topics

31.1 Synthesis of Ring-Fluorinated Heterocycles 31.2 Isotopically Labelled Heterocycles28 31.3 Bioprocesses in Heterocyclic Chemistry38 31.4 Green Chemistry 31.5 Ionic Liquids48 31.6 Applications and Occurrences of Heterocycles References

32 Heterocycles in Biochemistry; Heterocyclic Natural Products

32.1 Heterocyclic Amino Acids and Related Substances 32.2 Enzyme Co-Factors; Heterocyclic Vitamins; Co-Enzymes1 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 References

33 Heterocycles in Medicine

33.1 Mechanisms of Drug Actions3 33.2 The Neurotransmitters 33.3 Drug Discovery and Development 33.4 Heterocyclic Drugs4,5 33.5 Drugs Acting on the CNS 33.6 Anti-Infective Agents 33.7 Anti-Cancer Drugs 33.8 Photochemotherapy References

Index

← Prev
Back
Next →

← Prev
Back
Next →