Fluorine in heterocyclic chemistry volume 2 springerlink. Membered fluorinated heterocycles references pharmaceuticals containing fluorinated heterocyclic compounds fluorinated heterocyclic compounds wiley online library. Synthesis of fluorinated heterocyclic compounds and study of their interaction with dna. Kinetic study on the conversion of pyridine and quinolinecarboxylic acids to the corresponding trichloromethyl compounds. Waters defence science and technology laboratory, chemical and biological defence sciences, porton down, salisbury, wiltshire sp4 0jq, uk received. Photochemistry of fluorinated heterocyclic compounds. A photochemical synthesis of 3amino5perfluoroaryl1,2,4oxadiazoles.
Fluorinated heterocycles are becoming increasingly important in many areas including the pharmaceutical industry, materials science and agriculture. A photochemical approach to a synthesis of polyfluoroaryl1,2,4 triazoles. Synthesis of new fluorinated aminoheterocyclic compounds. A heterocyclic compound or ring structure is a cyclic compound that has atoms of at least two different elements as members of its rings. An expedient route for the synthesis of fluorinated 1,3,4oxadiazoles and 1,2,4triazoles cheminform 2004, 35 41 doi. A photochemical approach to a synthesis of polyfluoroaryl1,2,4triazoles. Pdf on oct 1, 2005, andrea pace and others published the synthesis of.
When the acid iia was heated with potassium fluoride in dimethylformamide, 3benzamido6,7,8,9tetrafluorocoumarin iii was formed. The cover feature reflects the fairy tale frau holle mother hulda from the famous book childrens and household tales collected by the brothers grimm. 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. In this paper, we report the preparation of these classes of heterocyclic compounds from fluorinated and trifluoromethylated1,3diketones as shown in scheme 1. 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. An expedient route for the synthesis of fluorinated 1,3,4oxadiazoles and 1,2,4triazoles. Heterocyclic chemistry is the branch of organic chemistry dealing with the synthesis, properties, and applications of these heterocycles.
Efficient onepot synthesis of novel fluorinated heterocycles using trimethylsilyl trifluoromethanesulfonate as a metalfree homogeneous lewis acid catalyst. Fluorine in heterocyclic chemistry volume 1 5membered. Synthesis of fluorinated heterocyclic compounds and study of. Heterocyclic compounds more than one hetero atom heterocyclic compounds one hetero atom organometallic and organometalloidal compounds. Abstract some more new fluorine substitutedamino compounds bearing. The cyclic part from greek kyklos, meaning circle of. Pdf heterocyclic chemistry download read online free. Heterocyclic derivatives, seen as a group, can be divided into two broad areas. A study has been made of the possibility of intramolecular cyclization of. Fluorine in heterocyclic chemistry volume 2 6membered. An expedient route to 5perfluoroalkyl1,2,4triazoles via an unusual hydrazinolysis of 5perfluoroalkyl1,2,4oxadiazoles. A thorough survey of synthetic methods, chemistry, and applications of major classes of fluorinated heterocycles.
A photochemical approach to a synthesis of fluorinated quinazolin4ones. 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. 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, new jersey, 2009. Pdf photochemistry of fluorinated heterocyclic compounds. Nicolo vivona, andrea pace, ivana pibiri, silvestre buscemi. Journal of heterocyclic chemistry 1978, 15 6, 893896. In addition, a recent monograph on general heterocyclic. A thorough survey of synthetic methods, chemistry, and applications of major classes of fluorinated heterocycles merging organic, heterocyclic, and fluoroorganic chemistry, fluorinated.
Journal of fluorine chemistry 1 2002 6578 fluorinated phosphorus compounds part 6. Sep 11, 2009 summary this chapter contains sections titled. 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. Journal of fluorine chemistry 107 2001 155158 fluorinated phosphorus compounds part 4. Fluorinated phosphorus compounds pdf free download. Aug 02, 2010 read fluorinated heterocyclic compounds.
It contains heterocyclic rings in various states of oxidation. It interferes with dna and rna synthesis by blocking the action of thymidylate synthetase, and. Heterocyclic chemistry is the branch of chemistry dealing with the synthesis, properties, and applications of heterocycles. Request pdf antiviral activity of fluorinated heterocyclic compounds introduction. Fluorinated heterocyclic compounds have many features which distinguish them from other corresponding halogenated compounds. Pdf fluorine in heterocyclic chemistry volume 2 researchgate. Synthesis, chemistry, and applications ebook written by viacheslav a. An effective strategy for the synthesis of fluorinated zoximes of 3perfluoroalkyl6phenyl2h1,2,4triazin 5ones via a ringenlargement reaction of 3benzoyl5perfluoroalkyl1,2,4oxadiazoles and hydrazine. On the other hand, requirements for the photostability andor photodegradation pattern of commercial fluorinated products under sunlight raise the question of the photoreactivity of.
Waters chemical and biological defence sector, defence evaluation and research agency, porton down, salisbury, wiltshire sp4 0jq, uk received 1 september 2000. Department of applied chemistry, faculty of engineering, okayama university, 3. Polyfluorinated heterocyclic compounds springerlink. Synthesis of fluorinated heterocycles sciencedirect. Fluorinated heterocyclic compounds by viacheslav a. Merging organic, heterocyclic, and fluoroorganic chemistry, fluorinated heterocyclic compounds have distinctively desirable properties suitable for use in pharmaceuticals and agrichemicals. Pharmaceuticals containing fluorinated heterocyclic compounds kenji uneyama department of applied chemistry, faculty of engineering, okayama university, 3. 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. These metrics are regularly updated to reflect usage leading up to the last few. 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. Compounds g8, g9, g26 suppressed hsv2bh reproduction by 50% at the concentrations of 56, 71 and 44 mgml, respectively.
Fluorinated heterocyclic compounds are widely employed in pharmaceuticals, agrochemicals, and new materials, and their synthesis constitutes an increasingly valuable research area. Download pdf principles of modern heterocyclic chemistry. This advanced textcumreference book presents a comprehensive account of the syntheses, reactions, properties and applications of all the most significant classes of heterocyclic compounds. Synthesis of fluorinated heterocyclic compounds and study. 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 chemistry university of nairobi personal websites. Pdf fluorinated heterocyclic compounds download ebook. Antiviral activity of fluorinated heterocyclic compounds. Pdf fluorinated heterocyclic compounds download ebook for free.
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. This is the first book in its class solely devoted to fluorinated heterocyclic compounds. Membered heterocycles containing oxygen, sulfur, selenium, and phosphorus atoms nmr spectra and structure of. Fluorine in heterocyclic chemistry volume 1 springerlink. A lack of anticholinesterase activity for four tris. 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. Heterocyclic compounds bearing emergent fluorinated substituents bruno commare 1, etienne schmitt 1.
Barton, the invention of reactions useful for the synthesis of specifically fluorinated natural products, pure and applied chemistry, 10. When naming such compounds the side of the heterocyclic ring is labeled by the letters a, b, c, etc. Department of chemistry, faculty of science, king abdul. Fluorinated heterocyclic compounds methylpyridines. Pdf w links390k add to acs chemworx sponsored access preface.
Read fluorinated heterocyclic compounds online, read in mobile or kindle. Download for offline reading, highlight, bookmark or take notes while you read fluorinated heterocyclic compounds. Fluorinated heterocycles are important building blocks in pharmaceutical, agrochemical and material sciences. Benzene, its derivatives, and condensed benzenoid compounds. View enhanced pdf access article on wiley online library html view download pdf for offline viewing. 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. 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. The front cover shows an allegory of the formation of polydopamine black material from dopamine white. The presence of fluorine can result in substantial functional changes in the biological as well as physicochemical properties of organic compounds. Nucleophilic fluorination in water can be considered as the holy grail of not only the chemistry of fluoroheterocyclic compounds, but also general organic fluorine. Membered heterocycles by attack of an external bidentate nucleophile. Fluorinated heterocyclic compounds fluorinated heterocyclic compounds synthesis, chemistry, and applications edited b.
Sep 11, 2009 a thorough survey of synthetic methods, chemistry, and applications of major classes of fluorinated heterocycles. Pharmaceuticals containing fluorinated heterocyclic compounds. Download fluorinated heterocyclic compounds ebook free in pdf and epub format. A photochemical approach to a synthesis of fluorinated quinazolin4ones article in heterocycles 3544 july 2004 with 59 reads. 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. Different water solubilising side chains were introduced to some of the successfully synthesised fluorinated heteroarenes to improve water solubility and potential biological activity. Pdf the synthesis of fluorinated heteroaromatic compounds. Pdf the data on the chemistry of fluorinated quinolines available in the literature of the last 1015 years are presented. 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. Fluorinated heterocyclic compounds wiley online books. Xray crystal structures of over 10 compounds were obtained including those of two macrocyclic compounds containing 21 and 24membered rings.
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