About the Book
This is the first book in its class solely devoted to fluorinated heterocyclic compounds. It encompasses all aspects of chemistry and applications of fluoroheterocycles including synthesis, biological activity studies, development of PET radiopharmaceuticals, structural NMR research, computational chemistry and many other critical areas. The book covers all major classes of heterocycles (azoles, azines, heteroalicyclic compounds, fused systems) as well as all
popular fluorine-containing fragments (C-F, N-F, CF2 CF3, OCF3, SF5). Particular attention was given to modern synthetic methods including metallocomplex catalysis and combinatorial chemistry, as applied to the chemistry of fluorinated heterocyclic compounds. The first chapter is devoted to critical
overview of the current status of the field and its historical perspective. The subject matter in subsequent chapters is divided into two broad areas. Chapters 2-7 focus on methods of preparation of several classes of fluorinated heterocycles. Included in synthetic methodologies reviewed are those based on selective fluorination, functionalization of fluorinated heterocycles, and the use of fluorinated building blocks. Chapters 8-15 deal with several aspects of research on biologically
significant fluorinated heterocycles and include reviews of synthetic approaches, structural studies, and applications. The breadth of topics together with the in depth treatment given to each topic will make this book a valuable resource for chemists of many disciplines.
Table of Contents:
PREFACE
Overview
1. Gakh, A. A.; Kirk, K. L. Fluorinated heterocycles.
Synthetic Methods and Building Blocks
2. Schlosser, M.; Borel, A.; Patiny, L. Site selective functionalization of fluorinated nitrogen heterocyles.
3. Umemoto, T. Preparation, Reactivity and Applications of N-Fluoropyridinium Salts.
4. Prakash, G. K. S.: Panja, C.; Do, C.; Bychinskaya, I.; Vaghoo, H.; Mathew, T.; Olah, G. A. Efficient One-Pot Synthesis of Novel Fluorinated Heterocycles Using Trimethylsilyl trifluoromethanesulfonate as a Metal-Free Homogeneous Lewis Acid Catalyst.
5. Sun, H.; Koch, A. S.; DiMagno, S. G. Rapid Preparation of Fluorinated Aromatic Heterocycles.
6. Petrov, V. A. Cycloaddition Reactions of Hexafluorothioacetone and Halogenated Thiocarbonyl Compounds. Chemical Transformations of Fluorinated Sulfur-Containing Heterocycles.
7. Arimitsu, S.; Hammond, G. B. Synthesis of gem-difluorinated heterocycles using a difluoropropargyl molecular scaffold.
Biologically Oriented Molecules, Synthesis
8. Welch, J. T.; Lim, D. Pentafluorosulfanyl serotonin analogs: synthesis, characterization and biological activity.
9. Fustero, S.; Sanz-Cervera, J. F.; Simón-Fuentes, A.; Román, R.; Catalán, S.; Murguía, M. New Fluorinated Pyrazol and Uracil Derivatives: Synthesis and Biological Activity.
10. Ashique, R.; Chirakal, R.; Schrobilgen, G. J.; Hughes, D. W.; Farncombe, T.; Gulenchyn, K.; Labiris, R.; Truman, T.; Saab, C. Reactivity and Selectivity of F2 Towards 3,4,6-Tri-O-acetyl-D-Glucal in Anhydrous HF: Synthesis of [18F]2-Fluoro-2-deoxy-?-D-allose and Its Use for the Detection of Breast Tumor.
10. Ashique, R.; Chirakal, R.; Schrobilgen, G. J.; Hughes, D. W.; Farncombe, T.; Gulenchyn, K.; Labiris, R.; Truman, T.; Saab, C. Reactivity and Selectivity of F2 Towards 3,4,6-Tri-O-acetyl-D-Glucal in Anhydrous HF: Synthesis of [18F]2-Fluoro-2-deoxy-?-D-allose and Its Use for the Detection of Breast Tumor.
11. Barchi, J. J., Jr. Structural Studies of Biologically Interesting Fluorinated Nucleosides.
12. Shestopalov, A. M.; Rodinovskaya, L. A.; Shestopalov, A. A.; Gromova, A. V.; Fedorov, A. E.; Gakh, A. A. Synthesis and reactions of fluorinated nicotinonitriles.
13. Brovarets, V.S.; Mityukhin, O.P.; Golovchenko, A.V.; Drach, B.S. Syntheses of fluorinated 1,3-oxazoles, 1,3,4-oxadiazoles, 1,3,4-thiadiazoles and oxazolo[4,5-d]pyrimidines.
14. Zlotin, S. G.; Kislitsin, P. G.; Astratyev, A. A.; Gakh, A. A. Synthetic Utilization of Polynitroaromatic Compounds. Synthesis of Fluorinated Fused Heterocycles from Polynitroaromatic Compounds.
15. Vovk, M. V.; Pinchuk, O. M.; Sukach, V. A.; Tolmachov, A. O.; Gakh, A. A. Trifluoromethoxy containing azoles and azines: synthesis and biological activity.
About the Author :
Andrei A. Gakh is a senior research scientist at Oak Ridge National Laboratory. His current research interests include chemistry of heterocyclic, fluoroorganic and nitro compounds as well as molecular engineering and nanotechnology. Kenneth L. Kirk was Chief of the Laboratory of Bioorganic Chemistry at the National Institute of Diabetes and Digestive and Kidney Diseases NIDDK between 1997 and 2008. His research interests have
focused on biomedicinal aspects of organofluorine chemistry.
