Advances in Heterocyclic Chemistry

Heterocyclic Chemistry in the 21st Century: A Tribute to Alan Katritzky
 
 
Academic Press
  • 1. Auflage
  • |
  • erschienen am 20. Juli 2016
  • |
  • 364 Seiten
 
E-Book | ePUB mit Adobe DRM | Systemvoraussetzungen
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978-0-12-805439-0 (ISBN)
 
Advances in Heterocyclic Chemistry is the definitive series in the field-one of great importance to organic chemists, polymer chemists, and many biological scientists. Because biology and organic chemistry increasingly intersect, the associated nomenclature also is being used more frequently in explanations. Written by established authorities in the field from around the world, this comprehensive review combines descriptive synthetic chemistry and mechanistic insight to yield an understanding of how chemistry drives the preparation and useful properties of heterocyclic compounds.
  • Considered the definitive serial in the field of heterocyclic chemistry
  • Serves as the go-to reference for organic chemists, polymer chemists, and many biological scientists
  • Provides the latest comprehensive reviews written by established authorities in the field
  • Combines descriptive synthetic chemistry and mechanistic insight to enhance understanding of how chemistry drives the preparation and useful properties of heterocyclic compounds
0065-2725
  • Englisch
  • San Diego
  • |
  • USA
Elsevier Science
  • 15,81 MB
978-0-12-805439-0 (9780128054390)
0128054395 (0128054395)
weitere Ausgaben werden ermittelt
  • Front Cover
  • Heterocyclic Chemistry in the 21st Century: A Tribute to Alan Katritzky
  • EDITORIAL ADVISORY BOARD
  • Heterocyclic Chemistry in the 21st Century: A Tribute to Alan Katritzky
  • Copyright
  • Contents
  • CONTRIBUTORS
  • PREFACE
  • One - SF5-Substituted Aromatic Heterocycles
  • 1. INTRODUCTION
  • 2. SYNTHESIS OF SF5-SUBSTITUTED AROMATIC HETEROCYCLES FROM SF5-SUBSTITUTED BENZENES
  • 2.1 Indoles and Indolines
  • 2.2 Benzothiophenes and Dibenzothiophenes
  • 2.3 Benzimidazoles
  • 2.4 Benzothiazole
  • 2.5 Benzisoxazoles
  • 2.6 Benzotriazoles
  • 2.7 Quinolines
  • 2.8 Quinoxalines and Quinazolines
  • 2.9 Benzopyrans (Chromenes)
  • 2.10 Phenothiazines
  • 3. SYNTHESIS OF SF5-SUBSTITUTED AROMATIC HETEROCYCLES FROM SF5CL (SF5BR): APPLICATION OF SF5-SUBSTITUTED ALKENES AND SF5-SUBST ...
  • 3.1 Pyrroles and Thiophenes
  • 3.2 Furans and Isobenzofuran
  • 3.3 Pyrazoles
  • 3.4 Isoxazoles and Isoxazolines
  • 3.5 1,2,3-Triazoles
  • 3.6 Thieno[3,4-b]thiophene
  • 4. SYNTHESIS OF SF5-SUBSTITUTED PYRIDINES BY OXIDATIVE FLUORINATION OF THEIR SULFUR SUBSTITUENT
  • 5. CONCLUSIONS
  • REFERENCES
  • Two - Synthesis of Aromatic Heterocycles Using Ring-Closing Metathesis
  • 1. INTRODUCTION
  • 2. FURANS AND PYRROLES
  • 2.1 Ring-Closing Metathesis Followed by Oxidation
  • 2.2 Ring-Closing Metathesis Followed by Elimination of a Leaving Group
  • 2.2.1 Path A: Mixed Acetal Route to Furans and Pyrroles
  • 2.2.2 Path B: Enol Ether Route to Furans
  • 3. BENZOFURANS, INDOLES, AND BENZIMIDAZOLES
  • 4. PYRIDINES, PYRIDONES, AND PYRIDAZINES
  • 4.1 Ring-Closing Metathesis Followed by Oxidation
  • 4.2 Ring-Closing Metathesis Followed by Elimination of a Leaving Group
  • 4.2.1 Path A: Synthesis of 2-Pyridones and 2-Pyridyl Triflates
  • 4.2.2 Path B: Synthesis of 3-Pyridones and 2-Hydroxypyridines
  • 5. QUINOLINES
  • 6. NATURAL PRODUCT SYNTHESIS
  • 6.1 Synthesis of Phytoalexine (Sophora Compound I)
  • 6.2 Synthesis of (-)-(Z)-Deoxypukalide
  • 6.3 Synthesis of (±)-Streptonigrin
  • 6.4 Synthesis of Citreofuran
  • REFERENCES
  • Three - Multicomponent Syntheses of Heterocycles Initiated by Catalytic Generation of Ynones and Ynediones
  • 1. INTRODUCTION
  • 2. CATALYTIC GENERATION OF ALKYNONES
  • 3. MULTICOMPONENT COUPLING-CYCLOADDITION SEQUENCES VIA ALKYNONE INTERMEDIATES
  • 3.1 Triazoles
  • 3.2 Isoxazoles
  • 4. MULTICOMPONENT COUPLING-ADDITION-CYCLOCONDENSATION SEQUENCES VIA ALKYNONE INTERMEDIATES
  • 4.1 Pyrroles
  • 4.2 Indoxyls
  • 4.3 Pyrazoles
  • 4.4 Pyridones
  • 4.5 a-Carbolines
  • 4.6 Pyrimidines
  • 4.7 Quinolines
  • 4.8 Quinolones
  • 4.9 Oxazoles
  • 4.10 Chromones
  • 4.11 Thiophenes
  • 4.12 Thiochromenones
  • 4.13 Benzothiazepines
  • 5. MULTICOMPONENT COUPLING-ADDITION-CYCLOCONDENSATION SEQUENCES VIA PROPIOLATE INTERMEDIATES
  • 6. CATALYTIC GENERATION OF ALKYNEDIONES AND MULTICOMPONENT COUPLING-ADDITION-CYCLOCONDENSATION SEQUENCES VIA YNEDIONE INTERMED ...
  • 7. CONCLUSION AND OUTLOOK
  • REFERENCES
  • Four - Metal-Catalyzed Coupling with Heterocycles
  • 1. INTRODUCTION
  • 2. THREE-MEMBERED HETEROCYCLES
  • 3. THIOPHENE AND BENZOTHIOPHENES
  • 4. FURANS AND BENZOFURANS
  • 5. PYRROLES
  • 6. INDOLES AND INDAZOLES
  • 7. IMIDAZOLES AND BENZIMIDAZOLES
  • 8. THIAZOLES AND BENZOTHIAZOLES
  • 9. OXAZOLES AND BENZOXAZOLES
  • 10. PYRIDINES AND PYRIMIDINES
  • 11. ISOQUINOLINES AND QUINOLONES
  • 12. MISCELLANEOUS HETEROCYCLES
  • ACKNOWLEDGMENT
  • REFERENCES
  • Five - A Journey Through Metal-Catalyzed CH Functionalization of Heterocycles: Insights and Trends
  • 1. INTRODUCTION
  • 2. C-H FUNCTIONALIZATION IN HETEROCYCLES: THE REGIOSELECTIVITY C-H ACTIVATION ENIGMA
  • 2.1 Nature's Finest: Innate Reactivity of Heterocycles
  • 2.2 Substrate Controlled: Influencing the Electronics with Substituents
  • 2.3 Substrate Controlled: Orchestrated Regioselectivity by Coordinating Moieties
  • 2.4 Catalyst Controlled: Influence of the Catalyst System on the Reaction Outcome
  • 3. CROSS-DEHYDROGENATIVE COUPLINGS: WHERE LESS IS MORE!
  • 3.1 Carbon-Carbon Bond Formation via Cross-Dehydrogenative Coupling
  • 3.1.1 Innate Reactivity in Cross Dehydrogenative Coupling
  • 3.1.2 Substrate Controlled Directing Groups in Cross-Dehydrogenative Coupling Reactions
  • 3.1.3 Catalyst-Controlled Directing Groups in Cross-Dehydrogenative Coupling Reactions
  • 3.2 Carbon-Heteroatom Bond Formation via Cross-Dehydrogenative Coupling
  • 4. CONCLUSIONS
  • ACKNOWLEDGMENTS
  • REFERENCES
  • Six - Progress in Heterocyclic Metallosupramolecular Construction
  • 1. INTRODUCTION
  • 2. MACROCYCLES
  • 3. 3D/CAGE
  • 4. METALLOMOLECULAR INTERCONVERSIONS
  • 5. MATERIALS
  • 6. MONOLAYER SHEETS
  • 7. CONCLUSIONS
  • ACKNOWLEDGMENTS
  • REFERENCES
  • Seven - QSAR of Heterocyclic Compounds in Large Descriptor Spaces
  • 1. INTRODUCTION
  • 2. MOLECULAR DESCRIPTORS
  • 2.1 Structural Descriptors
  • 2.2 Quantum Chemical Descriptors
  • 3. SELECTION OF THE BEST STATISTICAL QSAR MODELS IN LARGE DESCRIPTOR SPACES
  • 3.1 QSAR Development Based on Linear Methods. BMLR Method
  • 3.2 QSAR Development Based on Machine Learning Methods
  • 4. CODESSA PROJECT
  • 5. QSAR/QSPR APPLICATIONS IN LARGE DESCRIPTORS SPACES
  • 5.1 Physical and Physicochemical Properties
  • 5.1.1 Boiling Point
  • 5.1.2 Melting Point
  • 5.1.3 Viscosity
  • 5.1.4 Density of Organic Liquids
  • 5.1.5 Dielectric Constants
  • 5.1.6 Vapor Pressure
  • 5.2 Chemical Reactivity
  • 5.2.1 Gas Phase Homolysis
  • 5.2.2 Critical Micelle Concentration
  • 5.2.3 UV Spectral Intensities
  • 5.2.4 Stability Constants
  • 5.2.5 Acid Dissociation Constants
  • 5.2.6 Chain Transfer Constants
  • 5.2.7 Flash Point
  • 5.3 Biological Activity
  • 6. CONCLUSIONS
  • ACKNOWLEDGMENTS
  • REFERENCES
  • Eight - Developments in Heterocyclic Microwave Chemistry
  • 1. INTRODUCTION
  • 2. ROLE OF MICROWAVE IRRADIATION IN HETEROCYCLIC RING CLOSURES
  • 2.1 Five-Membered Heterocycles
  • 2.1.1 Five-Membered Heterocycles with One Heteroatom
  • 2.1.2 Five-Membered Heterocycles with Two Heteroatoms
  • 2.1.3 Five-Membered Heterocycles with More than Two Heteroatoms
  • 2.2 Six-Membered Heterocycles
  • 2.3 Fused Heterocycles
  • 2.3.1 Five-Membered Heterocycles Fused with Five-Membered Heterocyclic Systems
  • 2.3.2 Five-Membered Heterocycles Fused with Six-Membered Carbocyclic Systems
  • 2.3.3 Five-Membered Heterocycles Fused with Six-Membered Heterocyclic Systems
  • 2.3.4 Six-Membered Heterocycles Fused with Six-Membered Carbocyclic Systems
  • 2.3.5 Six-Membered Heterocycles Fused with Six-Membered Heterocyclic Systems
  • 2.3.6 Medium Ring Size Heterocycles Fused with Other Heterocyclic Systems
  • 2.4 Miscellaneous
  • 3. CONCLUSION
  • REFERENCES
  • Nine - Calculating the Aromaticity of Heterocycles
  • 1. INTRODUCTION
  • 2. OUTLINE OF THE MOST FREQUENTLY USED AROMATICITY DESCRIPTORS
  • 2.1 Energetic Aromaticity Descriptors
  • 2.2 Geometry-Based Descriptors
  • 2.3 Magnetic Measures
  • 2.4 Electronic Indices
  • 3. DIFFERENCES BETWEEN CARBO- AND HETEROCYCLIC p-ELECTRON SYSTEMS
  • 4. AROMATICITY OF NUCLEOBASES
  • 5. CYCLIC HETERO-p-ELECTRON SYSTEMS AS TEST PROBES FOR STATISTICAL MULTIDIMENSIONALITY OF AROMATICITY CHARACTERISTICS
  • 6. CONCLUSIONS
  • ACKNOWLEDGMENTS
  • REFERENCES
  • Index
  • A
  • B
  • C
  • D
  • E
  • F
  • G
  • H
  • I
  • K
  • L
  • M
  • N
  • O
  • P
  • Q
  • R
  • S
  • T
  • U
  • V
  • W
  • X
  • Y
  • Z
  • Back Cover

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