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| Biography | |
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| Abbreviations | |
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| Introduction to Second Edition | |
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| Heterocyclic Nomenclature | |
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| Six-membered aromatic heterocycles | |
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| Five-membered aromatic heterocycles | |
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| Non-aromatic heterocycles | |
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| Small-ring heterocycles | |
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| Structures of Heteroaromatic Compounds | |
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| Structures of benzene and naphthalene | |
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| Structures of pyridines and pyridiniums | |
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| Structures of quinolines and isoquinolines | |
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| Structures of diazines (illustrated using pyrimidine) | |
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| Structures of pyrroles, thiophenes and furans | |
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| Structure of indoles | |
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| Structures of azoles (illustrated using imidazole) | |
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| Common Reaction Types in Heterocyclic Chemistry | |
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| Introduction | |
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| Acidity and basicity | |
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| Electrophilic substitution of aromatic molecules | |
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| Nucleophilic substitution of aromatic molecules | |
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| Radical substitution of heterocycles | |
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| C-Metallated heterocycles as nucleophiles | |
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| Generation of C-metallated heterocycles | |
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| Dimethylformamide dimethyl acetal (DMFDMA) | |
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| Formation and hydrolysis of imine/enamine | |
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| Common synthetic equivalents of carbonyl compounds in ring synthesis | |
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| Cycloaddition reactions | |
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| Palladium in Heterocyclic Chemistry | |
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| Palladium(0)-catalysed (and related) reactions | |
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| Addition to alkenes: the Heck reaction | |
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| Carbonylation reactions | |
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| Cross-coupling reactions between heteroatom nucleophiles and halides - making carbon-heteroatom bonds | |
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| Triflates as substrates for palladium-catalysed reactions | |
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| Mechanisms of palladium(0)-catalysed processes | |
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| Reactions involving electrophilic palladation | |
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| Copper-catalysed amination | |
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| Selectivity | |
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| Pyridines | |
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| Electrophilic addition to nitrogen | |
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| Electrophilic substitution at carbon | |
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| Nucleophilic substitution | |
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| Nucleophilic addition to pyridinium salts | |
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| C-metallated pyridines | |
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| Palladium(0)-catalysed reactions | |
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| Oxidation and reduction | |
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| Pericyclic reactions | |
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| Alkyl and carboxylic acid substituents | |
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| Oxygen substituents | |
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| N-Oxides | |
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| Amine substituents | |
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| Ring synthesis - disconnections | |
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| Synthesis of pyridines from 1,5-dicarbonyl compounds | |
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| Synthesis of pyridines from an aldehyde, two equivalents of a 1,3-dicarbonyl compound and ammonia | |
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| Synthesis of pyridines from 1,3-dicarbonyl compounds and a C2N unit | |
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| Exercises | |
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| Diazines | |
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| Electrophilic addition to nitrogen | |
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| Electrophilic substitution at carbon | |
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| Nucleophilic substitution | |
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| Radical substitution | |
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| C-Metallated diazines | |
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| Palladium(0)-catalysed reactions | |
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| Pericyclic reactions | |
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| Oxygen substituents | |
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| N-Oxides | |
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| Amine substituents | |
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| Ring synthesis - disconnections | |
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| Synthesis of pyridazines from 1,4-dicarbonyl compounds | |
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| Synthesis of pyrimidines from 1,3-dicarbonyl compounds | |
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| Synthesis of pyrazines from 1,2-dicarbonyl compounds | |
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| Synthesis of pyrazines from -amino-carbonyl compounds | |
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| Benzodiazines | |
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| Exercises | |
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| Quinolines and Isoquinolines | |
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| Electrophilic addition to nitrogen | |
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| Electrophilic substitution at carbon | |
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| Nucleophilic substitution | |
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| Nucleophilic addition to quinolinium/isoquinolinium salts | |
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| C-Metallated quinolines and isoquinolines | |
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| Palladium(0)-catalysed reactions | |
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| Oxidation and reduction | |
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| Alkyl substituents | |
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| Oxygen substituents | |
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| N-Oxides | |
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| Ring synthesis - disconnections | |
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| Synthesis of quinolines from anilines | |
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| Synthesis of quinolines from ortho-aminoaryl ketones or aldehydes | |
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| Synthesis of isoquinolines from 2-arylethamines | |
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| Synthesis of isoquinolines from aryl-aldehydes and an aminoacetaldehyde acetal | |
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| Synthesis of isoquinolines from ortho-alkynyl aryl-aldehydes or corresponding imines | |
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| Exercises | |
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| Pyryliums, Benzopyryliums, Pyrones and Benzopyrones | |
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| Pyrylium salts | |
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| Electrophiles | |
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| Nucleophilic addition | |
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| Ring-opening reactions of 2H-pyrans | |
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| Oxygen substituents - pyrones and benzopyrones | |
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| Ring synthesis of pyryliums from 1,5-diketones | |
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| Ring synthesis of 4-pyrones from 1,3,5-triketones | |
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| Ring synthesis of 2-pyrones from 1,3-keto-aldehydes | |
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| Ring synthesis of 1-benzopyryliums, coumarins and chromones | |
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| Exercises | |
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| Pyrroles | |
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| Electrophilic substitution at carbon | |
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| N-Deprotonation and N-metallated pyrroles | |
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| C-Metallated pyrroles | |
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| Palladium(0)-catalysed reactions | |
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| Oxidation and reduction | |
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| Pericyclic reactions | |
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| Reactivity of side-chain substituents | |
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| The 'pigments of life' | |
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| Ring synthesis - disconnections | |
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| Synthesis of pyrroles from 1,4-dicarbonyl compounds | |
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| Synthesis of pyrroles from -amino-ketones | |
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| Synthesis of pyrroles using isocyanides | |
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| Exercises | |
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| Indoles | |
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| Electrophilic substitution at carbon | |
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| N-Deprotonation and N-metallated indoles | |
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| C-Metallated indoles | |
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| Palladium(0)-catalysed reactions | |
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| Oxidation and reduction | |
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| Pericyclic reactions | |
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| Reactivity of side-chain substituents | |
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| Oxygen substituents | |
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| Ring synthesis - disconnections | |
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| Synthesis of indoles from arylhydrazones | |
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| Synthesis of indoles from ortho-nitrotoluenes | |
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| Synthesis of indoles from ortho-aminoaryl alkynes | |
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| Synthesis of indoles from ortho-alkylaryl isocyanides | |
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| Synthesis of indoles from ortho-acyl anilides | |
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| Synthesis of isatins from anilines | |
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| Synthesis of oxindoles from anilines | |
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| Synthesis of indoxyls from anthranilic acids | |
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| Azaindoles | |
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| Exercises | |
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| Furans and Thiophenes | |
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| Electrophilic substitution at carbon | |
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| C-Metallated thiophenes and furans | |
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| Palladium(0)-catalysed reactions | |
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| Oxidation and reduction | |
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| Pericyclic reactions | |
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| Oxygen substituents | |
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| Ring synthesis - disconnections | |
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| Synthesis of furans and thiophenes from 1,4-dicarbonyl compounds | |
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| Exercises | |
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| 1,2-Azoles and 1,3-Azoles | |
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| Introduction | |
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| Electrophilic addition to N | |
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| Electrophilic substitution at C | |
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| Nucleophilic substitution of halogen | |
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| N-Deprotonation and N-metallated imidazoles and pyrazoles | |
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| C-Metallated N-substituted imidazoles and pyrazoles, and C-metallated thiazoles and isothiazoles | |
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| C-Deprotonation of oxazoles and isoxazoles | |
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| Palladium(0)-catalysed reactions | |
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| Reductions | |
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| Pericyclic reactions | |
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| Oxygen and amine substituents | |
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| Synthesis of thiazoles and imidazoles from -halo-ketones | |
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| Synthesis of 1,3-azoles from 1,4-dicarbonyl compounds | |
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| Synthesis of 1,3-azoles using tosylmethyl isocyanide | |
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| Synthesis of 1,3-azoles via dehydrogenation | |
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| Synthesis of pyrazoles and isoxazoles from 1,3-dicarbonyl compounds | |
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| Synthesis of isoxazoles and pyrazoles from alkynes | |
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| Synthesis of isothiazoles from -amino , -unsaturated carbonyl compounds | |
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| Exercises | |
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| Purines | |
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| Electrophilic addition to nitrogen | |
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| Electrophilic substitution at carbon | |
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| N-Deprotonation and N-metallated purines | |
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| Oxidation | |
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| Nucleophilic substitution | |
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| C-Metallated purines by direct deprotonation or halogen-metal exchange | |
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| Palladium(0)-catalysed reactions | |
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| Purines with oxygen and amine substituents | |
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| Ring synthesis - disconnections | |
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| Synthesis of purines from 4,5-diaminopyrimidines | |
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| Synthesis of purines from 5-aminoimidazole-4-carboxamide | |
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| 'One-step syntheses' | |
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| Exercises | |
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| Heterocycles with More than Two Heteroatoms: Higher Azoles (5-Membered) and Higher Azines (6-Membered) | |
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| Higher Azoles | |
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| Introduction | |
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| Higher azoles containing nitrogen as the only ring heteroatom: triazoles, tetrazole and pentazole | |
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| Benzotriazole | |
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| Higher azoles also containing ring sulfur or oxygen: oxa- and thiadiazoles | |
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| Higher azines | |
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| Exercises | |
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| Heterocycles with Ring-Junction Nitrogen (Bridgehead Nitrogen) | |
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| Introduction | |
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| Indolizine | |
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| Azaindolizines | |
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| Synthesis of indolizines and azaindolizines | |
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| Quinoliziniums and quinolizinones | |
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| Heteropyrrolizines (pyrrolizines containing additional heteroatoms) | |
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| Cyclazines | |
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| Exercises | |
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| Non-Aromatic Heterocycles | |
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| Introduction | |
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| Three-membered rings | |
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| Four-membered rings | |
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| Five- and six-membered rings | |
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| Ring synthesis | |
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| Heterocycles in Nature | |
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| Heterocyclic -amino acids and related substances | |
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| Heterocyclic vitamins - co-enzymes | |
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| Porphobilinogen and the 'Pigments of Life' | |
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| Deoxyribonucleic acid (DNA), the store of genetic information, and ribonucleic acid (RNA), its deliverer | |
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| Heterocyclic secondary metabolites | |
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| Heterocycles in Medicine | |
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| Medicinal chemistry - how drugs function | |
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| Drug discovery | |
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| Drug development | |
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| The neurotransmitters | |
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| Histamine | |
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| Acetylcholine (ACh) | |
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| Anticholinesterase agents | |
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| Adrenaline and noradrenaline | |
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| Other significant cardiovascular drugs | |
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| Drugs acting specifically on the CNS | |
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| Other enzyme inhibitors | |
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| Anti-infective agents | |
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| Antiparasitic drugs | |
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| Antibacterial drugs | |
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| Antiviral drugs | |
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| Anticancer drugs | |
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| Photochemotherapy | |
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| Applications and Occurrences of Heterocycles in Everyday Life | |
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| Introduction | |
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| Dyes and pigments | |
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| Polymers | |
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| Pesticides | |
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| Explosives | |
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| Food and drink | |
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| Heterocyclic chemistry of cooking | |
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| Natural and synthetic food colours | |
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| Flavours and fragrances (F&F) | |
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| Toxins | |
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| Electrical and electronic | |
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| Index | |