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. Pharmaceuticals containing fluorinated heterocyclic compounds. A photochemical approach to a synthesis of fluorinated quinazolin4ones. Synthesis of new fluorinated aminoheterocyclic compounds. Fluorine in heterocyclic chemistry volume 1 springerlink. Fluorinated heterocyclic compounds are widely employed in pharmaceuticals, agrochemicals, and new materials, and their synthesis constitutes an increasingly valuable research area. Antiviral activity of fluorinated heterocyclic compounds. Pdf heterocyclic chemistry download read online free. Synthesis, chemistry, and applications ebook written by viacheslav a. Abstract some more new fluorine substitutedamino compounds bearing.
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. Pharmaceuticals containing fluorinated heterocyclic compounds kenji uneyama department of applied chemistry, faculty of engineering, okayama university, 3. 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. An expedient route to 5perfluoroalkyl1,2,4triazoles via an unusual hydrazinolysis of 5perfluoroalkyl1,2,4oxadiazoles. Heterocyclic derivatives, seen as a group, can be divided into two broad areas. In this paper, we report the preparation of these classes of heterocyclic compounds from fluorinated and trifluoromethylated1,3diketones as shown in scheme 1. 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. Nucleophilic fluorination in water can be considered as the holy grail of not only the chemistry of fluoroheterocyclic compounds, but also general organic fluorine. 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. Pdf photochemistry of fluorinated heterocyclic compounds.
Membered fluorinated heterocycles references pharmaceuticals containing fluorinated heterocyclic compounds fluorinated heterocyclic compounds wiley online library. 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. When the acid iia was heated with potassium fluoride in dimethylformamide, 3benzamido6,7,8,9tetrafluorocoumarin iii was formed. Synthesis of fluorinated heterocyclic compounds and study of. Pdf the data on the chemistry of fluorinated quinolines available in the literature of the last 1015 years are presented. 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. An expedient route for the synthesis of fluorinated 1,3,4oxadiazoles and 1,2,4triazoles cheminform 2004, 35 41 doi. Pdf fluorinated heterocyclic compounds download ebook for free. 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, new jersey, 2009. Download fluorinated heterocyclic compounds ebook free in pdf and epub format. Heterocyclic compounds bearing emergent fluorinated substituents bruno commare 1, etienne schmitt 1. Merging organic, heterocyclic, and fluoroorganic chemistry, fluorinated heterocyclic compounds have distinctively desirable properties suitable for use in pharmaceuticals and agrichemicals. 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.
Many pharmaceuticals and agrochemicals contain at least one heterocyclic unit. A photochemical approach to a synthesis of fluorinated quinazolin4ones article in heterocycles 3544 july 2004 with 59 reads. Fluorinated heterocycles are becoming increasingly important in many areas including the pharmaceutical industry, materials science and agriculture. Fluorinated heterocyclic compounds fluorinated heterocyclic compounds synthesis, chemistry, and applications edited b. Membered heterocycles containing oxygen, sulfur, selenium, and phosphorus atoms nmr spectra and structure of. Waters chemical and biological defence sector, defence evaluation and research agency, porton down, salisbury, wiltshire sp4 0jq, uk received 1 september 2000. 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. On the other hand, requirements for the photostability andor photodegradation pattern of commercial fluorinated products under sunlight raise the question of the photoreactivity of. Fluorine in heterocyclic chemistry volume 2 springerlink. Journal of fluorine chemistry 107 2001 155158 fluorinated phosphorus compounds part 4. Fluorinated heterocycles are important building blocks in pharmaceutical, agrochemical and material sciences.
The cover feature reflects the fairy tale frau holle mother hulda from the famous book childrens and household tales collected by the brothers grimm. View enhanced pdf access article on wiley online library html view download pdf for offline viewing. Journal of heterocyclic chemistry 1978, 15 6, 893896. An effective strategy for the synthesis of fluorinated zoximes of 3perfluoroalkyl6phenyl2h1,2,4triazin5ones via a ringenlargement reaction of 3benzoyl5perfluoroalkyl1,2,4oxadiazoles and hydrazine. Heterocyclic compounds more than one hetero atom heterocyclic compounds one hetero atom. In addition, a recent monograph on general heterocyclic. Department of applied chemistry, faculty of engineering, okayama university, 3. A study has been made of the possibility of intramolecular cyclization of. Heterocyclic chemistry is the branch of organic chemistry dealing with the synthesis, properties, and applications of these heterocycles. Fluorinated phosphorus compounds pdf free download. Xray crystal structures of over 10 compounds were obtained including those of two macrocyclic compounds containing 21 and 24membered rings. Download pdf principles of modern heterocyclic chemistry. A lack of anticholinesterase activity for four tris. Barton, the invention of reactions useful for the synthesis of specifically fluorinated natural products, pure and applied chemistry, 10.
An effective strategy for the synthesis of fluorinated zoximes of 3perfluoroalkyl6phenyl2h1,2,4triazin 5ones via a ringenlargement reaction of 3benzoyl5perfluoroalkyl1,2,4oxadiazoles and hydrazine. Fluorinated heterocyclic compounds wiley online books. A photochemical synthesis of 3amino5perfluoroaryl1,2,4oxadiazoles. 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.
A photochemical approach to a synthesis of polyfluoroaryl1,2,4 triazoles. Benzene, its derivatives, and condensed benzenoid compounds. These metrics are regularly updated to reflect usage leading up to the last few. Heterocyclic chemistry is the branch of chemistry dealing with the synthesis, properties, and applications of heterocycles. When naming such compounds the side of the heterocyclic ring is labeled by the letters a, b, c, etc. Pdf fluorinated heterocyclic compounds download ebook. Heterocyclic compounds more than one hetero atom heterocyclic compounds one hetero atom organometallic and organometalloidal compounds.
Fluorine in heterocyclic chemistry volume 1 5membered. Synthesis of fluorinated heterocyclic compounds and study of their interaction with dna. A thorough survey of synthetic methods, chemistry, and applications of major classes of fluorinated heterocycles merging organic, heterocyclic, and fluoroorganic chemistry, fluorinated. This twovolume work combines comprehensive information on the chemistry of the fluorinated heterocycles. 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. It contains heterocyclic rings in various states of oxidation. A heterocyclic compound or ring structure is a cyclic compound that has atoms of at least two different elements as members of its rings. The cyclic part from greek kyklos, meaning circle of. An expedient route for the synthesis of fluorinated 1,3,4oxadiazoles and 1,2,4triazoles. Pdf the synthesis of fluorinated heteroaromatic compounds. Short, efficient routes towards the synthesis of fluorinated nitrogen. Request pdf antiviral activity of fluorinated heterocyclic compounds introduction.
Read fluorinated heterocyclic compounds online, read in mobile or kindle. A variety of aldehydes, including aromatic, aliphatic and heterocyclic examples, could be. Photochemistry of fluorinated heterocyclic compounds. Polyfluorinated heterocyclic compounds springerlink. Synthesis of fluorinated heterocyclic compounds and study. Journal of fluorine chemistry 1 2002 6578 fluorinated phosphorus compounds part 6.
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. Fluorinated heterocyclic compounds methylpyridines. Aug 02, 2010 read fluorinated heterocyclic compounds. Membered heterocycles by attack of an external bidentate nucleophile. 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. Fluorine in heterocyclic chemistry volume 2 6membered. Sep 11, 2009 a thorough survey of synthetic methods, chemistry, and applications of major classes of fluorinated heterocycles.
Sep 11, 2009 summary this chapter contains sections titled. Pdf w links390k add to acs chemworx sponsored access preface. Pdf fluorine in heterocyclic chemistry volume 2 researchgate. This is the first book in its class solely devoted to fluorinated heterocyclic compounds.
A photochemical approach to a synthesis of polyfluoroaryl1,2,4triazoles. Download for offline reading, highlight, bookmark or take notes while you read fluorinated heterocyclic compounds. Heterocyclic chemistry university of nairobi personal websites. 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 heterocycles sciencedirect.
It interferes with dna and rna synthesis by blocking the action of thymidylate synthetase, and. Fluorinated heterocyclic compounds by viacheslav a. The presence of fluorine can result in substantial functional changes in the biological as well as physicochemical properties of organic compounds. Synthesis of new fluorinated amino heterocyclic compounds bearing 6aryl5oxo1,2,4triazin3yl moiety as antimicrobial agents. A thorough survey of synthetic methods, chemistry, and applications of major classes of fluorinated heterocycles. Nicolo vivona, andrea pace, ivana pibiri, silvestre buscemi. Kinetic study on the conversion of pyridine and quinolinecarboxylic acids to the corresponding trichloromethyl compounds. Different water solubilising side chains were introduced to some of the successfully synthesised fluorinated heteroarenes to improve water solubility and potential biological activity. 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. The front cover shows an allegory of the formation of polydopamine black material from dopamine white. All perfluoroheteroaromatic compounds are weak bases a fluorine atom placed ortho to. Fluorinated heterocyclic compounds have many features which distinguish them from other corresponding halogenated compounds.
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