Heterocyclic Chemistry at a Glance

ISBN-10: 0470971215

ISBN-13: 9780470971215

Edition: 2nd 2012

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Description: This expanded second edition provides a concise overview of the main principles and reactions of heterocyclic chemistry for undergraduate students studying chemistry and related courses. Using a successful and student–friendly "at a glance" approach, this book helps the student grasp the essence of heterocyclic chemistry, ensuring that they can confidently use that knowledge when required. The chapters are thoroughly revised and updated with references to books and reviews; extra examples and student exercises with answers online; and color diagrams that emphasize exactly what is happening in the reaction chemistry depicted.

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Book details

List price: $29.95
Edition: 2nd
Copyright year: 2012
Publisher: John Wiley & Sons, Limited
Publication date: 10/12/2012
Binding: Paperback
Pages: 230
Size: 8.50" wide x 12.00" long x 0.50" tall
Weight: 1.210
Language: English

John Joule is Professor of Organic Chemistry at the University of Manchester and Keith Mills was, until his recent early retirement, a research scientist at GlaxoSmithKline in Stevenage.

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