http://www.loc.gov/mods/v3 http://www.loc.gov/standards/mods/v3/mods-3-2.xsd
Advances in Heterocyclic Chemistry, Volume 123 brings together the fields of biology and organic chemistry, highlighting the ways they increasingly intersect. This updated volume includes a section on new developments in tetrazole chemistry, a section on the synthesis and applications of thiophene derivatives as organic materials, and a synopsis of the properties and applications on heteroaromatic rings in medicinal chemistry. Written by established authorities 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.This definitive series in the field will be of great value to organic chemists, polymer chemists and many biological scientists.- 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 as 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 chemistry.
Front Cover -- Advances in Heterocyclic Chemistry -- EDITORIAL ADVISORY BOARD -- Advances in Heterocyclic ChemistryEditorsERIC F. V. SCRIVENDepartment of Chemistry, University of Florida, Gainesville, FL, ... -- Contents -- CONTRIBUTORS -- PREFACE -- One -- Developments in Tetrazole Chemistry (2009-16) -- 1. INTRODUCTION -- 2. FUNDAMENTAL ASPECTS AND THEORETICAL CALCULATIONS -- 2.1 Electronic Structure and Geometry -- 2.2 Protolytic Equilibria -- 2.3 Thermochemical and Explosive Properties -- 2.4 Azido-Tetrazole Isomerism -- 2.5 Bioisosterism and Biological Modeling -- 3. SYNTHESIS AND REACTIVITY OF TETRAZOLES -- 3.1 1H-Unsubstituted Tetrazoles -- 3.2 1-Substituted- and 1,5-Disubstituted Tetrazoles -- 3.3 2-Substituted and 2,5-Disubstituted Tetrazoles -- 3.4 Tetrazoles with a Fused Ring -- 3.5 Functionalization of Tetrazoles -- 3.6 Metal Ion Complexes With a Tetrazole Moiety -- 4. IMPORTANT COMPOUNDS AND APPLICATIONS -- 4.1 Biologically Active Derivatives -- 4.1.1 Antiviral Activity -- 4.1.2 Anticancer Agents -- 4.1.3 Antibacterials -- 4.1.4 Antifungal -- 4.1.5 Antioxidants -- 4.1.6 Receptor Antagonists of the Central Nervous System -- 4.1.7 Inhibitors of Metabolic Processes -- 4.2 Medicines With a Tetrazole Moiety -- 4.2.1 Hypotensive Action -- 4.2.2 Antihistamine Agents -- 4.2.3 Action on the Central Nervous System -- 4.2.4 Antimicrobial and Antiinflammatory Activity -- 4.3 Energetic Tetrazoles -- 4.4 Materials With Tetrazole as an Active Component -- 4.4.1 Polymer Membranes -- 4.4.2 Other Polymer Materials -- 4.4.3 Nanomaterials -- 4.4.4 Catalysts -- 4.4.5 Corrosion Inhibitors -- 5. CONCLUDING REMARKS -- ACKNOWLEDGMENT -- REFERENCES -- Two -- The Synthesis and Chemistry of Azolobenzodiazepines -- 1. INTRODUCTION -- 2. IMIDAZOBENZODIAZEPINES -- 3. PYRROLOBENZODIAZEPINES -- 4. PYRAZOLOBENZODIAZEPINES -- 5. TRIAZOLOBENZODIAZEPINES.
6. OXAZOLOBENZODIAZEPINES -- 7. TETRAZOLOBENZODIAZEPINES -- 8. CONCLUSIONS -- REFERENCES -- Three -- Synthesis and Applications of Thiophene Derivatives as Organic Materials -- 1. INTRODUCTION -- 2. SYNTHESIS OF OLIGO- AND POLYTHIOPHENES -- 2.1 Cross-Coupling Reactions -- 2.1.1 Stille Reaction -- 2.1.2 Suzuki Reaction -- 2.2 Direct Arylation -- 2.3 Sulfur Functionalization -- 2.4 Enabling Technologies -- 3. OLIGO- AND POLYTHIOPHENES IN ORGANIC (OPTO)ELECTRONICS -- 3.1 Organic Field-Effect Transistors -- 3.2 Photovoltaic Devices -- 4. THIOPHENE OLIGOMERS AS FLUORESCENT PROBES IN BIOLOGICAL SYSTEMS -- 4.1 Labeling of Proteins and DNA and Staining of Live Cells -- 4.2 Side-Chain Functionalized Quinquethiophenes as Optical Ligands for the Detection of Protein Aggregates Present in Neurodege ... -- 4.3 Physiologically Driven Coassembly of Oligothiophene Fluorophores With Specific Proteins Inside Live Cells -- 5. OLIGO/POLYTHIOPHENE-BASED NANOPARTICLES AND MICROFIBERS -- 6. CONCLUDING REMARKS -- REFERENCES -- Four -- Thiophene-Based Quinomethane Analogs -- 1. INTRODUCTION -- 2. 3-ALKYLIDENETHIOPHEN-2-ONES -- 2.1 Properties -- 2.1.1 Theoretical Methods -- 2.1.2 Experimental Structural Methods -- 2.1.2.1 X-Ray Diffraction -- 2.1.2.2 Nuclear Magnetic Resonance Spectroscopy -- 2.1.2.3 Infrared, Ultraviolet-Vis Spectroscopy and Photochemical Properties -- 2.1.3 Thermodynamic Aspects: Tautomerism -- 2.2 Reactivity -- 2.2.1 Electrophilic Attack at Ring Carbon -- 2.2.2 Nucleophilic Attack at Ring Carbon -- 2.2.3 Nucleophilic Attack at Exocyclic Carbon -- 2.2.4 Diels-Alder Reactions -- 2.2.5 Miscellaneous -- 2.3 Synthesis -- 2.3.1 From 3H-Thiophen-2-ones -- 2.3.1.1 Condensation With Aldehydes and Ketones -- 2.3.1.2 Reaction With Other Electrophiles -- 2.3.1.3 Oxidation -- 2.3.2 From Thiophene-2,3-diones.
2.3.3 From Furan-2-ones or Thiophene-2-thiones by O/S Exchange -- 2.3.4 Dearomatization of Thiophenes -- 2.3.4.1 O-Dealkylation of 2-Alkoxythiophenes -- 2.3.4.2 From Thiophene-3-aldehydes -- 2.3.4.3 From 2-Lithiated Thiophenes -- 2.3.4.4 With Ring Opening/Ring Closure -- 2.3.5 From Acyclic Precursors -- 2.3.6 By Cycloreversion of a Bicyclic System -- 2.4 Applications -- 2.4.1 Uses in the Electronics Industry -- 2.4.2 Use as Dyes -- 2.4.3 Formation of Metal Complexes -- 2.4.4 Medicinal, Pharmaceutical, and Agrochemical Applications -- 3. 2-ALKYLIDENETHIOPHEN-3-ONES -- 3.1 Properties -- 3.1.1 Theoretical Methods -- 3.1.2 Experimental Structural Methods -- 3.1.2.1 X-Ray Diffraction -- 3.1.2.2 Nuclear Magnetic Resonance Spectroscopy -- 3.1.2.3 Infrared, Ultraviolet-Vis Spectroscopy and Mass Spectrometry -- 3.2 Reactivity -- 3.2.1 Nucleophilic Attack at Exocyclic Carbon -- 3.2.2 Cycloaddition Reactions -- 3.2.3 Miscellaneous -- 3.3 Synthesis -- 3.3.1 From 2H-Thiophen-3-ones -- 3.3.1.1 Condensation With Aldehydes and Ketones -- 3.3.1.2 Reaction With Other Electrophiles -- 3.3.1.3 Oxidation -- 3.3.2 From Thiophene-3-thiones by O/S Exchange -- 3.3.3 Dearomatization of Thiophenes -- 3.3.4 From Acyclic Precursors -- 3.3.5 By Cycloreversion of a Bicyclic System -- 3.3.6 Ring Expansion/Ring Contraction of S-Containing Heterocycles -- 3.4 Applications -- 3.4.1 Uses in the Electronics Industry -- 3.4.2 Use as Dyes -- 3.4.3 Medicinal and Pharmaceutical Applications -- 4. 5-ALKYLIDENETHIOPHEN-2-ONES -- 4.1 Properties -- 4.1.1 Theoretical Methods -- 4.1.2 Experimental Structural Methods -- 4.1.2.1 X-Ray Diffraction -- 4.1.2.2 Nuclear Magnetic Resonance Spectroscopy -- 4.1.2.3 Infrared and Ultraviolet-Vis Spectroscopy -- 4.1.2.4 Dipole Moments -- 4.2 Reactivity -- 4.2.1 Electrophilic Attack at Ring Carbon -- 4.2.2 Nucleophilic Attack at Ring Carbon.
3.1 A Synopsis of Some Applications of H-Bonding Properties of Aromatic Heterocycles in Medicinal Chemistry -- 3.1.1 Intramolecular H-Bonds in Drug Design -- 3.1.2 Examples of Intermolecular H-Bonding in Drug-Target Interactions -- 3.2 Heterocycles and Metal Binding -- 3.2.1 Heterocycles and Iron Binding -- 3.2.2 Heterocycles and Zinc Binding -- 3.2.3 Heterocycles and Magnesium, Cobalt, and Manganese Binding -- 3.3 Applications of Electron Withdrawing Properties of Heterocycles in Medicinal Chemistry -- 3.3.1 Activated Carbonyl and Nitrile Derivatives as Protease and Hydrolase Inhibitors -- 3.3.2 Acidification of Exocyclic N and CH Atoms -- 3.4 Heterocycles and Nonbonded Interactions in Drug Design -- 3.4.1 Dipole-Dipole Interactions -- 3.4.2 Lone Pair-Lone Pair Interactions and Conformation -- 3.5 Special Properties of Sulfur-Containing Heterocycles and Applications in Drug Design -- 3.5.1 1,4-X to S interactions -- 3.5.2 1,5-X to S Interactions -- 3.5.3 1,6-X to S Interactions -- 3.5.4 Intermolecular O to S Interactions -- 4. EPILOGUE -- ACKNOWLEDGMENTS -- REFERENCES -- INDEX -- A -- B -- C -- D -- E -- F -- G -- H -- I -- J -- L -- M -- N -- O -- P -- Q -- R -- S -- T -- X -- Z -- Back Cover.
edited by Eric F.V. Scriven and Christopher A. Ramsden.
Advances in Heterocyclic Chemistry Volume 123