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Showing 1 to 16 of 16 for “"Aryne"”.
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New Methods in Aryne Chemistry
Arynes are important reactive intermediates in the synthesis of bioactive molecules and natural products, organic materials, catalysts, and polyaryl compounds. They are neutral, reactive, aromatic intermediates lacking two adjacent hydrogen atoms on an aromatic ring. They offer the strategic …
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Recent Advances in Indole Aryne Cycloaddition Chemistry. Part I: Total Synthesis of (±)-cis-Trikentrin B. Part II: Investigation into the Regioselectivity of 6,7-Indole Aryne Cycloadditions. Part III: Synthesis and Reactions of Novel Tribromoindoles
… in the Buszek laboratories in 2007, the indole arynes and their cycloaddition chemistry has demonstrated its significance in achieving the total synthesis of biologically active indole alkaloid natural products such as the trikentrins and herbindoles in a facile manner. The application of …
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Total synthesis of (±)-cis-trikentrin B, (±)-herbindole A and (±)-herbindole B. investigation into the regioselectivity of 6,7-Indole aryne cycloadditions
… A and (±)-herbindole B via intermolecular indole aryne cycloaddition are described. The 5,6,7-tribromoindole was synthesized via Leimgruber-Batcho indole synthesis protocols. The main question would be whether the key intermediate 5,6,7-tribromo-N-TBSindole would undergo selective metal-halogen …
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Part I. Computational, theoretical and synthetic studies of the indole arynes and their reactions. Part II. Computational, theoretical, and mechanistic studies of n-vinyltrialkylammonium, n-vinylpyridinium, and n-vinyldiazonium tetrafluoroborate salts.
… and first report by Buszek in 2007, Indole arynes have been established as an invaluable synthetic tool in the total synthesis of many complex natural products of biological and medicinal significance. Of particular interest are polyhaloindoles, which we have exploited for their synthetic …
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Novel Polycyclic Benzannulated Indole Scaffolds via Indole Aryne Cycloaddition, Pd (0)-Catalyzed Cross-coupling and ROM/RCM methodologies: Their Applications to Library Development and Drug Discovery
… subsequent elimination to give the 6,7-indole aryne which underwent Diels-Alder cycloadditions with cyclopentadiene, furan and 2,5-dimethyl furan. These cycloadducts were N-alkylated and then subjected to Grubb’s catalyst ring opening metathesis/ring closing metathesis to afford 12 unique 6,7- …
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Reactions of some non-enolisable chloroketones with amide ion and a new synthesis of acridones /|nGuo-shyoung John Chen. -- 260 St. Catharines, Ont. : [s. n.],
… deals mainly with historical studies on aryne chemistry and the Haller-Bauer reaction. Secti.on I i.s concerned with syntheses of 2-benzamido-2'chlorobenzophenone and 2-benzamido~3'-chlorobenzophenone,and with thei,r respective reactions wi.th potassium amide in ammonia. …
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Indole Arynes in organic synthesis : discovery and applications for the total synthesis of complex natural products
Arynes and heteroarynes are very important and useful reactive intermediates with many applications in organic synthesis, including natural products total synthesis. Although benzyne, the parent and most famous aryne, has itself been known for over 50 years, arynes derived from the ubiquitous …
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Strategies for the synthesis of bioactive compounds: biomimetic approaches to the Salinosporamides and the hexadehydro-Diels-Alder reaction
… between a diyne and an alkyne to form aryne reactive intermediate. In Part II we show the scope of substrates that are capable of generating an aryne via the HDDA reaction. Additionally, we show that HDDA-mediated generation of arynes allows for the discovery of new modes of aryne …
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Benzannulated indoles as drug discovery templates. Efforts towards the total synthesis of a library of therapeutic candidates inspired by Cis-Trikentrin A
… through the discovery of a new class of reactive aryne intermediates. These intermediates allow for the generation of an in-situ 6,7-indole aryne, proving readily susceptible to selective annulation of the indole via [4+2] cycloaddition. Additionally, the tunable selectivity of the indole aryne …
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Development of Nickel and Zirconium Mediated Cycloadditions for the Synthesis of Substituted Pentacene
… and sodium amalgam to produce a nickelaryne. Application of the [2+2+2] cycloaddition methodology to the longer nickel-aryne in the presence of a 1,3-diyne resulted in an iterative pathway for the synthesis of substituted pentacene. Preliminary efforts for the direct polymerization of …
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Synthesis and characterization of trinuclear metal clusters containing benzynechromium tricarbonylh
… moiety. This is the first example of an aryne to show such unsymmetrical bonding to a Ru3 system. The X-ray crystallographic analysis forRu3(C0)8[C6H4Cr(C0)3][43-PBut] reveals a novel type of benzyne structure, which contains a closed Ru3 framework with a symmetrical benzynechromium …
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Computational modeling of organic structure, spectra, and reactivity
… used to examine the regioselectivity of indole aryne cycloadditions and kinetic isotope effects of substituted anilines. The use of proton nucleomers to calculate linear free energy relationships to reduce both experimental and computational time is examined. A significant portion of this thesis …
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The functionalization of fullerenes and nanocarbon materials for photovoltaics and other applications
… solar cell performances by the addition of aryne-functionalized fullerenes to active layers as a minority component. In Chapter 6, we describe isoxazoline-functionalized fullerenes and carbon nanotubes and explore their transition metal complexes. Co(II) and Fe(II) complexes on carbon …
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In Pursuit of Extraordinarily Twisted Acenes
… reaction conditions necessary to generate the aryne. Although quite successful, this approach suffers from many drawbacks including low overall yields, difficulty in derivatization, and lack of scalability. The focus of the dissertation is the application of an alternative synthetic approach to …
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Reactions of various aromatic nitro-compounds and anthraquinones with selected bases and nucleophiles
… on deals mainly with hi storical studies on aryne chemi stry and ring closure via arynes , hydride replacement from aromatic rings by nucleophi les, c l eavage of anthr aquinones in basic medium and the Leuckart reaction . This work can be divided into two main s ect i ons. Section I is …
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Some chemistry of bromobenzopyrans
… as a result of the trapping of the heteroaryne, 3,4-didehydro-2H[ 1 ]ben zopyran. This reaction constitutes the generation of a novel aryne. Diels-Alder adducts obtained by the use of 2,5-dimethylfuran and 1,3-diphenylisobenzofuran have been aromatised providing facile access to …