A thorough survey of synthetic methods, chemistry, and applications of major classes of fluorinated heterocycles merging organic, heterocyclic, and fluoroorganic chemistry, fluorinated. Heterocyclic derivatives, seen as a group, can be divided into two broad areas. A photochemical synthesis of 3amino5perfluoroaryl1,2,4oxadiazoles. Fluorinated heterocycles are becoming increasingly important in many areas including the pharmaceutical industry, materials science and agriculture. Polyfluorinated heterocyclic compounds springerlink. Pdf heterocyclic chemistry download read online free.
A study has been made of the possibility of intramolecular cyclization of. Heterocyclic compound, any of a major class of organic chemical compounds characterized by the fact that some or all of the atoms in their molecules are joined in rings containing at least one atom of an element other than carbon c. Pdf on oct 1, 2005, andrea pace and others published the synthesis of. Efficient onepot synthesis of novel fluorinated heterocycles using trimethylsilyl trifluoromethanesulfonate as a metalfree homogeneous lewis acid catalyst. This twovolume work combines comprehensive information on the chemistry of the fluorinated heterocycles. Fluorine in heterocyclic chemistry volume 2 springerlink. A kinetic study and other mechanistic details will be published separately 5b preliminary studies indicate substantial cytoxicity toward plant and animal cell lines below pyr 10. A photochemical approach to a synthesis of polyfluoroaryl1,2,4 triazoles. The cyclic part from greek kyklos, meaning circle of. Journal of fluorine chemistry 107 2001 155158 fluorinated phosphorus compounds part 4.
On the other hand, requirements for the photostability andor photodegradation pattern of commercial fluorinated products under sunlight raise the question of the photoreactivity of. The cover feature reflects the fairy tale frau holle mother hulda from the famous book childrens and household tales collected by the brothers grimm. Journal of heterocyclic chemistry 1978, 15 6, 893896. Pharmaceuticals containing fluorinated heterocyclic compounds kenji uneyama department of applied chemistry, faculty of engineering, okayama university, 3. Membered heterocycles by attack of an external bidentate nucleophile. When the acid iia was heated with potassium fluoride in dimethylformamide, 3benzamido6,7,8,9tetrafluorocoumarin iii was formed. Abstract some more new fluorine substitutedamino compounds bearing. Read fluorinated heterocyclic compounds online, read in mobile or kindle. Aug 02, 2010 read fluorinated heterocyclic compounds. Request pdf antiviral activity of fluorinated heterocyclic compounds introduction. Fluorinated heterocyclic compounds are widely employed in pharmaceuticals, agrochemicals, and new materials, and their synthesis constitutes an increasingly valuable research area.
These metrics are regularly updated to reflect usage leading up to the last few. A thorough survey of synthetic methods, chemistry, and applications of major classes of fluorinated heterocyclesmerging organic, heterocyclic, and fluoroorganic chemistry, fluorinated heterocyclic compounds have distinctively desirable properties suitable for use in pharmaceuticals and agrichemicals, especially their ability to penetrate the cell membrane barrier for drug absorption. The incorporation of fluorine or fluorinated moieties into organic compounds plays a key role in life scienceoriented research, as it can often result in profound changes to the physicochemical and biological properties of the resulting compounds. It contains heterocyclic rings in various states of oxidation. This advanced textcumreference book presents a comprehensive account of the syntheses, reactions, properties and applications of all the most significant classes of heterocyclic compounds. A photochemical approach to a synthesis of fluorinated quinazolin4ones. Heterocyclic compounds bearing emergent fluorinated substituents bruno commare 1, etienne schmitt 1. Sep 11, 2009 summary this chapter contains sections titled.
An expedient route for the synthesis of fluorinated 1,3,4oxadiazoles and 1,2,4triazoles. It interferes with dna and rna synthesis by blocking the action of thymidylate synthetase, and. Synthesis, chemistry, and applications ebook written by viacheslav a. Waters chemical and biological defence sector, defence evaluation and research agency, porton down, salisbury, wiltshire sp4 0jq, uk received 1 september 2000. This is the first book in its class solely devoted to fluorinated heterocyclic compounds.
Photochemistry of fluorinated heterocyclic compounds. Kinetic study on the conversion of pyridine and quinolinecarboxylic acids to the corresponding trichloromethyl compounds. Fluorine in heterocyclic chemistry volume 2 6membered. A growing interest in fluorinated heterocycles owing to their applications in industrial or pharmaceutical areas currently prompts development of new synthetic methodologies for targeted compounds.
A photochemical approach to a synthesis of polyfluoroaryl1,2,4triazoles. An expedient route for the synthesis of fluorinated 1,3,4oxadiazoles and 1,2,4triazoles cheminform 2004, 35 41 doi. Journal of fluorine chemistry 1 2002 6578 fluorinated phosphorus compounds part 6. Membered fluorinated heterocycles references pharmaceuticals containing fluorinated heterocyclic compounds fluorinated heterocyclic compounds wiley online library. Synthesis of new fluorinated amino heterocyclic compounds bearing 6aryl5oxo1,2,4triazin3yl moiety as antimicrobial agents. This second volume in the series is an essential tool not only for advanced undergraduates and graduates, but also for academic and industrial researchers in. A thorough survey of synthetic methods, chemistry, and applications of major classes of fluorinated heterocycles.
Pdf fluorinated heterocyclic compounds download ebook for free. In this paper, we report the preparation of these classes of heterocyclic compounds from fluorinated and trifluoromethylated1,3diketones as shown in scheme 1. Pdf fluorinated heterocyclic compounds download ebook. Fluorine in heterocyclic chemistry volume 1 5membered. Department of chemistry, faculty of science, king abdul. Many pharmaceuticals and agrochemicals contain at least one heterocyclic unit. 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. Nucleophilic fluorination in water can be considered as the holy grail of not only the chemistry of fluoroheterocyclic compounds, but also general organic fluorine. Merging organic, heterocyclic, and fluoroorganic chemistry, fluorinated heterocyclic compounds have distinctively desirable properties suitable for use in pharmaceuticals and agrichemicals. Membered heterocycles containing oxygen, sulfur, selenium, and phosphorus atoms nmr spectra and structure of. A heterocyclic compound or ring structure is a cyclic compound that has atoms of at least two different elements as members of its rings. Waters defence science and technology laboratory, chemical and biological defence sciences, porton down, salisbury, wiltshire sp4 0jq, uk received.
Nicolo vivona, andrea pace, ivana pibiri, silvestre buscemi. Download pdf principles of modern heterocyclic chemistry. In addition, a recent monograph on general heterocyclic. Sep 11, 2009 a thorough survey of synthetic methods, chemistry, and applications of major classes of fluorinated heterocycles. Fluorinated heterocycles are important building blocks in pharmaceutical, agrochemical and material sciences. A thorough survey of synthetic methods, chemistry, and applications of major classes of fluorinated heterocycles merging organic, heterocyclic, and fluoroorganic chemistry, fluorinated heterocyclic compounds have distinctively desirable properties suitable for use in pharmaceuticals and agrichemicals, especially their ability to penetrate the cell membrane barrier for drug absorption. When naming such compounds the side of the heterocyclic ring is labeled by the letters a, b, c, etc. Fluorinated heterocyclic compounds have many features which distinguish them from other corresponding halogenated compounds. Heterocyclic chemistry university of nairobi personal websites. Pdf w links390k add to acs chemworx sponsored access preface. Pdf photochemistry of fluorinated heterocyclic compounds. Department of applied chemistry, faculty of engineering, okayama university, 3. Synthesis of fluorinated heterocyclic compounds and study. An effective strategy for the synthesis of fluorinated zoximes of 3perfluoroalkyl6phenyl2h1,2,4triazin 5ones via a ringenlargement reaction of 3benzoyl5perfluoroalkyl1,2,4oxadiazoles and hydrazine.
Pdf fluorine in heterocyclic chemistry volume 2 researchgate. Synthesis of fluorinated heterocycles sciencedirect. Barton, the invention of reactions useful for the synthesis of specifically fluorinated natural products, pure and applied chemistry, 10. Fluorinated heterocyclic compounds, new jersey, 2009. The material has been divided such that the first volume is dedicated to 5membered fluorinated heterocycles and macrocycles, while the second volume combines data connected with the chemistry of fluorine containing 6membered heterocycles. Antiviral activity of fluorinated heterocyclic compounds.
A lack of anticholinesterase activity for four tris. The mechanism consists in the formation of intermediate 6 as a result of the reaction between the hydroxyl function and the fluoroiminium followed by the decomposition of intermediate 6 to afford the fluorinated product 7 and the corresponding fluorinated acetamide 4ac scheme 5. Heterocyclic compounds more than one hetero atom heterocyclic compounds one hetero atom organometallic and organometalloidal compounds. The front cover shows an allegory of the formation of polydopamine black material from dopamine white. Download fluorinated heterocyclic compounds ebook free in pdf and epub format. Fluorinated phosphorus compounds pdf free download. Pharmaceuticals containing fluorinated heterocyclic compounds. Fluorine in heterocyclic chemistry volume 1 springerlink. The presence of fluorine can result in substantial functional changes in the biological as well as physicochemical properties of organic compounds. A photochemical approach to a synthesis of fluorinated quinazolin4ones article in heterocycles 3544 july 2004 with 59 reads. Heterocyclic compounds more than one hetero atom heterocyclic compounds one hetero atom.
Heterocyclic chemistry is the branch of organic chemistry dealing with the synthesis, properties, and applications of these heterocycles. Fluorinated heterocyclic compounds methylpyridines. Pdf the synthesis of fluorinated heteroaromatic compounds. Download for offline reading, highlight, bookmark or take notes while you read fluorinated heterocyclic compounds. Xray crystal structures of over 10 compounds were obtained including those of two macrocyclic compounds containing 21 and 24membered rings. Fluorinated heterocyclic compounds by viacheslav a. Synthesis of new fluorinated aminoheterocyclic compounds. View enhanced pdf access article on wiley online library html view download pdf for offline viewing. Different water solubilising side chains were introduced to some of the successfully synthesised fluorinated heteroarenes to improve water solubility and potential biological activity.
An expedient route to 5perfluoroalkyl1,2,4triazoles via an unusual hydrazinolysis of 5perfluoroalkyl1,2,4oxadiazoles. The incorporation of fluorine or fluorinated moieties into organic compounds plays a key role in life scienceoriented research, as it can often result in profound changes to the physicochemical and biological properties of the resulting compounds 1. Pdf the data on the chemistry of fluorinated quinolines available in the literature of the last 1015 years are presented. Compounds g8, g9, g26 suppressed hsv2bh reproduction by 50% at the concentrations of 56, 71 and 44 mgml, respectively. Short, efficient routes towards the synthesis of fluorinated nitrogen. Benzene, its derivatives, and condensed benzenoid compounds. Synthesis of fluorinated heterocyclic compounds and study of. Some more new fluorine substitutedamino compounds bearing 6aryl5oxo1,2,4triazin3yl moieties and its derivatives 3 7 have been synthesised successfully from aroylation of 62aminophenyl3thioxo1,2,4triazin5one 1, followed by fluoro amination with 4fluoroanilinein abs etoh and then treated with ammoniaetoh and finally acylationaroylation or cyclocondensation reactions. Merging organic, heterocyclic, and fluoroorganic chemistry, fluorinated heterocyclic compounds have distinctively desirable properties suitable for use in pharmaceuticals and agrichemicals, especially their ability to penetrate the cell membrane barrier for drug absorption. An effective strategy for the synthesis of fluorinated zoximes of 3perfluoroalkyl6phenyl2h1,2,4triazin5ones via a ringenlargement reaction of 3benzoyl5perfluoroalkyl1,2,4oxadiazoles and hydrazine. Fluorinated heterocyclic compounds wiley online books.
Nucleoside analogues have a special place among the most effective antiviral drugs and the study of. Fluorinated heterocyclic compounds fluorinated heterocyclic compounds synthesis, chemistry, and applications edited b. Synthesis of fluorinated heterocyclic compounds and study of their interaction with dna. A variety of aldehydes, including aromatic, aliphatic and heterocyclic examples, could be. All perfluoroheteroaromatic compounds are weak bases a fluorine atom placed ortho to. Over fifty structurally diverse, novel fluorinated heteroarenes, have been successfully synthesised by snar reaction of a range of fluorinated arenes including pentafluoropyridine, hexafluorobenzene, and methyl pentafluorobenzoate by introduction of a range. Heterocyclic chemistry is the branch of chemistry dealing with the synthesis, properties, and applications of heterocycles.
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