| Description |
1 online resource |
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text txt rdacontent |
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computer c rdamedia |
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online resource cr rdacarrier |
| Contents |
Front Cover -- Advances in Heterocyclic Chemistry -- Copyright -- Contents -- Contributors -- Preface -- Chapter One: Recent advances in 1,2,4-triazolo[1,5-a]pyrimidine chemistry -- 1. Introduction -- 1.1. General survey -- 1.2. Scope and limitation -- 1.3. Nomenclature -- 2. Occurrence and synthesis -- 2.1. Survey -- 2.2. Occurrence -- 2.3. Syntheses from 5-amino-1,2,4-triazoles and 1,3-biselectrophiles -- 2.3.1. Principle and conditions -- 2.3.2. The diversity of biselectrophiles -- 2.3.3. Regioselectivity -- 2.3.4. The direct synthesis of triazolopyrimidines substituted onto carbon ring atoms -- 2.3.5. The use of modified biselectrophiles -- 2.3.6. The use of polyfunctional electrophiles -- 2.3.7. Syntheses via dihydro triazolopyrimidines -- 2.3.8. Multicomponent reactions -- 2.3.9. Special syntheses -- 2.4. Syntheses using special aminotriazole derivatives -- 2.4.1. Syntheses of N-substituted triazolopyrimidines -- 2.4.2. The use of aminotriazole-based intermediates -- 2.5. Triazole ring syntheses -- 2.5.1. Syntheses from 1,2-diaminopyrimidines -- 2.5.2. Syntheses from N-(pyrimid-2-yl)amidine-series compounds -- 2.5.3. Syntheses from 2-hydrazinopyrimidines -- 2.5.4. Other triazole ring syntheses -- 2.6. Other routes to triazolopyrimidines -- 2.6.1. Aromatization of dihydro derivatives -- 2.6.2. Ring transformation and cleavage -- 3. Structure -- 3.1. Theoretical methods -- 3.2. X-ray diffraction -- 3.3. Molecular spectra -- 3.3.1. H NMR spectra -- 3.3.2. C NMR spectra -- 3.3.3. F NMR spectra -- 3.3.4. Electronic spectra -- 3.3.5. Infrared and Raman spectra -- 3.3.6. Mass spectra -- 3.4. Physicochemical properties -- 3.5. Tautomerism -- 4. Reactivity -- 4.1. Triazolopyrimidines as bases and acids -- 4.1.1. Protonation and dissociation -- 4.1.2. Coordination -- 4.2. Alkylation at nitrogen ring atoms -- 4.3. Carbon-carbon coupling at ring atoms. |
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4.3.1. The use of organometallic and metal salt reagents -- 4.3.2. Suzuki coupling -- 4.3.3. Sonogashira coupling -- 4.3.4. Oxidative coupling -- 4.3.5. Reductive coupling -- 4.3.6. Nucleophilic addition -- 4.4. Other reactions at ring atoms -- 4.5. Nucleophilic substitution of functional groups at the rings -- 4.5.1. Substitution of halogen -- 4.5.2. Substitution of oxygen-, sulfur-, or nitrogen-containing functions -- 4.6. Transformation of individual substituents -- 4.6.1. Oxygen- or sulfur-containing groups -- 4.6.2. Amines and their derivatives -- 4.6.3. Carbonyl containing groups -- 4.7. Ring cleavage and recyclization -- 4.8. Anellation of heterocyclic rings -- 4.8.1. Anellation onto 6/7 positions -- 4.8.2. Anellation onto other positions -- 4.9. Reactivity of side chains -- 4.9.1. Reactions involving halogen or oxygen functionalities -- 4.9.2. Reactions involving sulfur, nitrogen, or phosphorus functionalities -- 4.9.3. Formation of hydrocarbon groups -- 4.9.4. Formation of diheterocyclyl compounds -- 5. Application -- 5.1. Pharmaceutical use -- 5.2. Agrochemical use -- 5.3. Optical and information recording uses -- 5.4. Other uses -- References -- Chapter Two: Fluorescent heterocycles: Recent trends and new developments -- 1. Introduction -- 2. Furans and benzofurans: Sustainable fluorophores -- 3. Si-rhodamines: Xanthenes and silicon united -- 4. 4H-imidazoles: Brightness and darkness combined -- 5. Imidazolinones: The chromophore of the GFP -- 6. Thiazoles: Learning from firefly -- 7. Oxazoles and benzoxazoles: More than scintillators and optical brighteners -- 8. Oxadiazoles and benzoxadiazoles: From antiretroviral drugs to omni functional fluorophores -- 9. Quinolizinium salts: Water-soluble isoelectronic analogous of anthracene -- 10. Acridines and acridones: Beyond acridine orange. |
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11. Triazines: Toward fluorescent covalent organic frameworks -- 12. Tetrazines: Fluorescent biorthogonal labeling -- 13. Imidazopyridines: Efficient ESIPT dyes -- 14. Imidazoquinoxalines: High quantum yields for blue OLEDs -- 15. Azaacenes: High-tech materials for organic electronics -- 16. Concluding remarks -- Acknowledgments -- References -- Chapter Three: Recent developments in the synthesis of the BODIPY dyes -- 1. Introduction -- 2. Synthesis of the BODIPY core -- 2.1. Synthesis of symmetrical BODIPYs -- 2.1.1. From pyrroles and acid anhydrides -- 2.1.2. From pyrroles and acid chlorides -- 2.1.3. From pyrroles and orthoesters -- 2.1.4. From pyrroles and thiophosgenes -- 2.1.5. From pyrroles and aldehydes, with subsequent oxidation -- 2.2. Synthesis of unsymmetrical BODIPYs -- 2.2.1. From pyrroles and 2-ketopyrroles -- 2.3. Boron chelation of dipyrromethenes -- 3. Updates on classical modifications of the BODIPY core -- 3.1. Electrophilic aromatic substitutions -- 3.1.1. SEAr of BODIPYs, 2/6-substitution -- 3.1.2. SEAr of dipyrromethanes, 3/5-substitution -- 3.2. Nucleophilic aromatic substitutions -- 3.2.1. SNAr of BODIPYs, 3/5-substitution with O-centered nucleophiles -- 3.2.2. SNAr of BODIPYs, 3/5-substitution with N-centered nucleophiles -- 3.2.3. SNAr of BODIPYs, 3/5-substitution with C-centered nucleophiles -- 3.2.4. SNAr of BODIPYs, 3/5-substitution with chalcogen nucleophiles -- 3.2.5. SNAr of BODIPYs, 1,7-substitution -- 3.2.6. SNAr of BODIPYs, 8-substitution -- 3.3. Knoevenagel condensation of 3,5-dimethyl-substituted BODIPYs -- 3.4. Substitution at boron -- 3.4.1. Intermolecular substitution at boron, fluorine to carbon -- 3.4.2. Intramolecular substitution at boron, fluorine to oxygen -- 3.4.3. Intermolecular substitution at boron, fluorine to oxygen -- 3.4.4. Substitution at boron via BCl2-BODIPYs, fluorine to oxygen or nitrogen. |
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3.4.5. Reaction of dipyrromethenes with functionalized borons -- 3.5. Substitution of 8-thiomethyl groups -- 3.5.1. SNAr of 8-thiomethyl BODIPYs -- 3.5.2. Liebeskind-Srogl cross-coupling of 8-thiomethyl BODIPYs -- 3.5.3. Reduction of 8-thiomethyl BODIPYs -- 3.6. Palladium-catalyzed cross-coupling reactions of BODIPYs -- 3.6.1. Cross-coupling reactions of haloBODIPYs -- 3.6.2. Regioselectivity of palladium-catalyzed cross-couplings -- 3.6.3. Negishi cross-couplings reactions of haloBODIPYs -- 3.6.4. Cascade cross-coupling reactions, Suzuki-Miyaura-Knoevenagel -- 3.6.5. Palladium-catalyzed silylation of BODIPYs -- 3.6.6. Miyaura borylation of BODIPYs -- 4. New methods for modification of the BODIPY core -- 4.1. Transition metal-catalyzed direct CH functionalization -- 4.1.1. Direct CH functionalization of BODIPYs, 3/5-functionalization -- 4.1.2. Direct CH functionalization of BODIPYs, 2/6-functionalization -- 4.1.3. Miyaura-Ishiyama-Hartwig borylation of dipyrromethenes and BODIPYs -- 4.1.4. Direct CH functionalization/annulation of BODIPYs -- 4.1.5. Direct C(sp)H arylation of 8-methyl BODIPYs -- 4.2. Oxidative nucleophilic substitution of hydrogen -- 4.3. Vicarious nucleophilic substitution -- 4.4. Radical-mediated functionalization -- 4.4.1. Radical-mediated 3/5-alkylation -- 4.4.2. Radical-mediated 3,5-diamination -- 4.5. Oxidative dimerization -- 4.6. Aldol-like reactions of 8-methyl BODIPYs, functionalization at 8-methyl -- 4.7. Nucleophilic substitution of 8-chloromethyl BODIPYs, functionalization at 3/5-methyl -- 5. Conclusions -- References -- Chapter Four: Liquid crystalline derivatives of heterocyclic radicals -- 1. Introduction -- 2. Liquid crystalline derivatives of cyclic aminoxyl radicals -- 2.1. Derivatives of the 4,4-dimethyl-3-oxazolidinyloxyl (DOXYL) radical (A) -- 2.1.1. Molecular design vs liquid crystalline behavior. |
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2.1.2. Magnetic properties -- 2.2. Derivatives of the 2,2,6,6-tetramethyl-1-piperidynoxyl (TEMPO) radical (B) -- 2.2.1. Molecular design and synthesis of liquid crystalline derivatives -- 2.2.1.1. Rod-like mesogens -- 2.2.1.2. Bent-core mesogens -- 2.2.1.3. Dimesogens -- 2.2.1.4. Disc-shaped mesogens -- 2.2.1.5. Polymers -- 2.2.2. Magnetic properties -- 2.3. Derivatives of the 4,4,5,5-tetramethylimidazoline-1-oxyl-3-oxide (NIT) radical(C) -- 2.4. Derivatives of the 1-pyrrolidinyloxyl (PROXYL) radical (D) -- 2.4.1. Rod-like derivatives -- 2.4.1.1. Synthesis -- 2.4.1.2. Liquid crystalline behavior -- 2.4.2. Derivatives forming columnar phases -- 2.4.3. Magnetic properties -- 3. Liquid crystalline derivatives of the 6-oxoverdazyl (E) and 6-thioxoverdazyl radicals -- 3.1. 6-Oxoverdazyl and 6-thioxoverdazyl: Chemistry and properties -- 3.2. Liquid crystalline derivatives -- 3.2.1. Disc-shaped derivatives of the 6-oxoverdazyl -- 3.2.2. Bent-core and hockey-stick derivatives of 6-oxoverdazyl and 6-thioxoverdazyl -- 3.2.3. Extended half-disc derivatives of the 6-oxoverdazyl -- 3.2.4. Bent-core diradical derivatives of the 6-oxoverdazyl -- 3.3. Other properties of liquid crystalline derivatives of 6-oxoverdazyl -- 3.3.1. Magnetic properties -- 3.3.2. Electronic absorption spectroscopy -- 3.3.3. Semiconductive properties -- 4. Liquid crystalline derivatives of the 1,4-dihydrobenzo[e][1,2,4]triazin-4-yl radical (F and G) -- 4.1. Fundamental properties of the benzo[e][1,2,4]triazin-4-yl -- 4.2. Synthesis of benzo[e][1,2,4]triazin-4-yl derivatives -- 4.3. Liquid crystalline derivatives -- 4.3.1. Disc-like derivatives -- 4.3.2. Bent-core derivatives -- 4.4. Other properties of liquid crystalline derivatives of benzo[e][1,2,4]triazin-4-yl -- 4.4.1. Magnetic properties -- 4.4.2. Electronic absorption spectroscopy -- 4.4.3. Semiconductive properties. |
| Subject |
Heterocyclic chemistry.
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Heterocyclic compounds.
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Chimie des composés hétérocycliques.
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Composés hétérocycliques.
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Heterocyclic chemistry
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Heterocyclic compounds
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| Added Author |
Scriven, Eric F. V., editor.
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Ramsden, Christopher A., 1946- editor.
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| ISBN |
9780128171820 (e-book) |
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0128171820 |
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9780128171813 (hbk.) |
| Standard No. |
AU@ 000068483179 |
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