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Advances in Heterocyclic Chemistry, Volume 140 is the latest release in this definitive series in the field of heterocyclic chemistry, one of great importance to organic chemists, polymer chemists, and many biological scientists. 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. Chapters in this new release include The chemistry of citrazinic acid (2,6-dihydroxyisonicotinic acid), Aza-Diels-Alder Reaction in the Synthesis of Tetrahyroquinoline Structures, and more. Additional chapters delve into Recent Developments in the Synthesis of 4-, 5-, 6- and 7-Azaindoles, Fluoroheterocycle formation using fluoroalkynes and their synthetic equivalents, Advances in applications of dihydropyridines in organic chemistry, and Recent Developments in the Chemistry of Triphyrins (2.1.1). 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 insights to enhance understanding on how chemistry drives the preparation and useful properties of heterocyclic compounds.
Intro -- Advances in Heterocyclic Chemistry -- Copyright -- Contents -- Contributors -- Preface -- Chapter One: The chemistry of citrazinic acid (2,6-dihydroxyisonicotinic acid) -- 1. Introduction -- 1.1. General survey -- 1.2. Scope and limitation -- 1.3. Nomenclature -- 2. Synthesis -- 2.1. From citric acid or its trialkyl esters -- 2.2. From symmetric citric acid dialkyl esters -- 2.3. By other cyclizations -- 2.4. From pyridine derivatives -- 3. Structure -- 3.1. Theoretical methods -- 3.2. X-ray diffraction -- 3.3. Molecular spectra -- 3.3.1. C NMR, and EPR spectra -- 3.3.2. Electronic spectra -- 3.3.3. Infrared and Raman spectra -- 3.3.4. Mass spectra -- 3.4. Chromatographic methods -- 3.5. Physicochemical properties -- 3.6. Tautomerism -- 4. Reactivity -- 4.1. Acidity, salts, and complexes -- 4.2. Reactions of the carboxyl group -- 4.2.1. Synthesis of carboxylic acid derivatives -- 4.2.2. Synthesis of other 4-carbon-functional compounds -- 4.2.3. Other reactions -- 4.3. Reactions at 2 and 6 positions -- 4.3.1. Uniform and direct substitution -- 4.3.2. Uniform substitution via 2,6-dihalo intermediates -- 4.3.3. Selective and direct substitution at 2 or 6 position -- 4.3.4. Selective substitution via 2- or 6-halo intermediates -- 4.3.5. Other reactions -- 4.4. Reactions at the ring nitrogen atom -- 4.5. Reactions at 3/5 positions -- 4.5.1. Carbon-functional substituents -- 4.5.2. Halogen substituents -- 4.5.3. Amino-functional substituents -- 4.5.4. Azo substituents -- 4.6. Ring transformation and anellation -- 4.7. Other reactions -- 4.8. Citrazinic acid as a precursor -- 5. Applications -- 5.1. Pharmaceutical use -- 5.2. Agrochemical use and environmental behavior -- 5.3. Use in materials and processes -- 5.4. Dyes -- 5.5. Photographic use -- 5.6. Analytical use -- 5.7. Carbon dots and nanofibers -- References.
Chapter Two: Aza-Diels-Alder reactions in the synthesis of tetrahydroquinoline structures -- 1. Introduction -- 2. Synthesis of tetrahydroquinolines -- 2.1. Synthesis of substituted tetrahydroquinolines -- 2.2. Synthesis of fused-ring tetrahydroquinolines -- 2.3. Synthesis of spiro tetrahydroquinolines -- 3. Concluding remarks -- Acknowledgment -- References -- Chapter Three: Recent developments in the synthesis of 4-, 5-, 6- and 7-azaindoles -- 1. Introduction -- 2. Retrosynthetic approach -- 3. Azaindoles from monosubstituted pyridines -- 3.1. From aminopyridines and analogous: Fischer synthesis -- 3.2. From aminopyridines: Gassman synthesis -- 3.3. From aminopyridines: Bischler Synthesis -- 3.4. From aminopyridines and analogous: Hong synthesis -- 3.5. From nitropyridines: Bartoli synthesis -- 3.6. From alkyl pyridines and derivatives -- 4. From disubstituted pyridines -- 4.1. From ortho-methylaminopyridines: Madelung synthesis -- 4.2. From ortho-methylaminopyridines: Reissert synthesis -- 4.3. From ortho-halovinypyridines -- 4.4. From ortho-nitrovinylpyridines: Leimbruger Batcho synthesis -- 4.5. From ortho-aminohalopyridines -- 4.5.1. Sonogashira coupling and cyclization -- 4.5.2. Larock synthesis -- 4.5.3. The Cacchi reaction -- 4.5.4. Double bond formation and Heck reaction -- 4.5.5. Heck/Suzuki/Stille reaction and cyclization -- 5. From pyrroles -- 5.1. From aminopyrroles: Skraup synthesis -- 5.2. From aminopyrroles: Combes synthesis -- 5.3. From aminopyrroles: Hantzsch synthesis -- 5.4. From pyrroles: Picted-Spengler synthesis -- 5.5. From pyrroles: Pomeranz-Fritsch synthesis -- 5.6. From 2,3-disubstituted pyrroles: Type 1,5-DICO, 1,4-DICO synthesis -- 5.7. From pyrroles: Electrocyclic cyclization or cycloaddition reaction -- 6. Miscellanea -- 7. Conclusion -- References.
8.3. Spectroscopic properties -- 8.4. Manganese(I) complexes -- 8.5. Rhenium(I) complexes -- 8.6. Ruthenium(II) complexes -- 8.7. Platinum(II) and platinum(IV) complexes -- 8.8. Palladium(II) complexes -- 8.9. Iron(II) complexes -- 8.10. Iridium(III) complexes -- 8.11. Phosphorus(V) complexes -- 8.12. Miscellaneous triphyrin(2.1.1) complexes -- 9. Conclusions -- Acknowledgments -- Declaration of competing interest -- References -- Chapter Six: Recent advances in the synthesis of star-shaped molecules based on a 1,3,5-triazine core -- 1. Introduction -- 2. Specific synthesis of star-shaped molecules based on a 1,3,5-triazine core -- 2.1. Cyclotrimerization of benzonitrile derivatives -- 2.1.1. Thiophene -- 2.1.2. Thiophen-2-ylbenzene -- 2.2. Alkylation/arylation reaction -- 2.2.1. N-alkylation/arylation -- 2.2.1.1. Pyridin-2-ylmethylamine -- 2.2.1.2. Di-(2-pyridyl)amine -- 2.2.2. S-Alkylation -- 2.2.2.1. Thiadizole -- 2.2.3. O-alkylation/arylation -- 2.2.3.1. Pyrrole -- 2.2.3.2. Imidazole -- 2.2.3.3. Pyridine -- 2.2.3.4. 1,3-Benzodioxole -- 2.2.3.5. Coumarin -- 2.2.3.6. Quinoline -- 2.2.3.7. Dipyrrolo[1,2-c:2,1-f][1,3,2]diazaborinin -- 2.2.3.8. Triheteroaryloxytriazines as precursors for N-(heteroaryl) carbamates -- 2.2.3.9. Triheteroaryloxytriazines as precursors for cyanohetrocyles -- 2.3. Click reaction -- 2.3.1. Benzyl-/aryl-1,2,3-triazole -- 2.3.2. Aroyloxyphenyl-1,2,3-triazole -- 2.3.3. (1H-1,2,3-triazol-1-yl)tetrahydro-2H-pyran -- 2.3.4. 1,2,3-Triazole and boron dipyrromethene -- 2.3.5. 1,2,3-Triazole and di-styryl boron dipyrromethene -- 2.3.6. 1,2,3-Triazole and triethoxysilane -- 2.4. Condensation reaction -- 2.4.1. 1,2,4-Triazole -- 2.4.2. Bis(6-aminopyrimidinyl)methanes -- 2.4.3. Bis(indol-3-yl)methanes -- 2.4.4. Bis(3-methyl-1H-indol-2-yl-)methanes -- 2.4.5. Quinoline -- 2.4.6. Bis(4-hydroxycoumarinyl)methanes -- 2.4.7. Phenanthroline.
edited by Eric F.V. Scriven, Christopher A. Ramsden.
Includes bibliographical references at the end of each chapter and index.