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Relevant bibliographies by topics / Cyclisation

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Academic literature on the topic 'Cyclisation'

Author: Grafiati

Published: 4 June 2021

Last updated: 25 May 2024

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Journal articles on the topic "Cyclisation"

1

McBurney, Roy T., and John C. Walton. "Interplay of ortho- with spiro-cyclisation during iminyl radical closures onto arenes and heteroarenes." Beilstein Journal of Organic Chemistry 9 (June 4, 2013): 1083–92. http://dx.doi.org/10.3762/bjoc.9.120.

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Sensitised photolyses of ethoxycarbonyl oximes of aromatic and heteroaromatic ketones yielded iminyl radicals, which were characterised by EPR spectroscopy. Iminyls with suitably placed arene or heteroarene acceptors underwent cyclisations yielding phenanthridine-type products from ortho-additions. For benzofuran and benzothiophene acceptors, spiro-cyclisation predominated at low temperatures, but thermodynamic control ensured ortho-products, benzofuro- or benzothieno-isoquinolines, formed at higher temperatures. Estimates by steady-state kinetic EPR established that iminyl radical cyclisations onto aromatics took place about an order of magnitude more slowly than prototypical C-centred radicals. The cyclisation energetics were investigated by DFT computations, which gave insights into factors influencing the two cyclisation modes.

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Rodger, Robert T., Marlowe S. Graham, and Christopher S. P. McErlean. "Hyperconjomer stereocontrol of cationic polyene cyclisations." Organic & Biomolecular Chemistry 17, no. 37 (2019): 8551–60. http://dx.doi.org/10.1039/c9ob01364d.

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The stereochemical outcome of cationic polyene cyclisations of geranylbenzene derivatives is affected by the different reactivity of hyperconjomer intermediates. The synthesis of (±)-taiwaniaquinone G by a cationic polyene cyclisation is described.

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Braddock, D. Christopher, and John M. Brown. "Catalytic and Stoichiometric Lewis Acid Participation in Aldehyde Ene Cyclisations." Collection of Czechoslovak Chemical Communications 65, no. 5 (2000): 741–56. http://dx.doi.org/10.1135/cccc20000741.

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Racemic 2-isopropyl-2-methylhex-5-enal has been synthesised in order to probe ene cyclisations leading to menthol analogues. The objective was first to discover catalytic conditions for preferential cyclisation to the menthol rather than the neomenthol series and then to develop (dynamic) kinetic resolution procedures which afforded a single enantiomer of product. It was found that catalytic quantities of both Me2AlCl and a bulky methylaluminium bis(phenoxide) reagent gave products attributed to a Meerwein-Pondorff-Verley reaction. In this the aldehyde is reduced to a primary alcohol and the ene product oxidised to the corresponding α,β-unsaturated ketone. By contrast, a related bulky chloroaluminium reagent catalysed the ene cyclisation cleanly, but preferentially to the undesired neomenthyl stereoisomer.

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Parsons, Philip, Lewis Allen, Daniel Jones, Alex Padgham, James Pryke, Joseph McKenna, and Daniel O’Reilly. "Approaches to the Synthesis of Highly Substituted Aromatic and Fused Rings: Metal-Catalysed versus Thermal Cyclisation." Synthesis 50, no. 01 (November 27, 2017): 84–101. http://dx.doi.org/10.1055/s-0036-1590952.

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A domino reaction has been used for the construction of lactonamycin derivatives. This research led to a comparison study between palladium-mediated cascade cyclisations and thermal alkyne [2+2+2] cyclisations. A palladium-mediated cyclisation of alkenyl bromides with alkynes and furans has been shown to furnish highly substituted aromatic rings. Penta- and hexasubstituted aromatic rings have also been prepared by the thermolysis of suitably substituted alkynes under microwave conditions. Tetrasubstituted pyridines can also be prepared using nitriles instead of alkynes. This work will provide a new and interesting array of drug templates; mechanistic details are discussed for both reaction series.

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Taherali, Farhan, Nerisha Chouhan, Fanjin Wang, Sebastien Lavielle, Maryana Baran, Laura E. McCoubrey, Abdul W. Basit, and Vipul Yadav. "Impact of Peptide Structure on Colonic Stability and Tissue Permeability." Pharmaceutics 15, no. 7 (July 15, 2023): 1956. http://dx.doi.org/10.3390/pharmaceutics15071956.

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Most marketed peptide drugs are administered parenterally due to their inherent gastrointestinal (GI) instability and poor permeability across the GI epithelium. Several molecular design techniques, such as cyclisation and D-amino acid (D-AA) substitution, have been proposed to improve oral peptide drug bioavailability. However, very few of these techniques have been translated to the clinic. In addition, little is known about how synthetic peptide design may improve stability and permeability in the colon, a key site for the treatment of inflammatory bowel disease and colorectal cancer. In this study, we investigated the impact of various cyclisation modifications and D-AA substitutions on the enzymatic stability and colonic tissue permeability of native oxytocin and 11 oxytocin-based peptides. Results showed that the disulfide bond cyclisation present in native oxytocin provided an improved stability in a human colon model compared to a linear oxytocin derivative. Chloroacetyl cyclisation increased native oxytocin stability in the colonic model at 1.5 h by 30.0%, whereas thioether and N-terminal acetylated cyclisations offered no additional protection at 1.5 h. The site and number of D-AA substitutions were found to be critical for stability, with three D-AAs at Tyr, Ile and Leu, improving native oxytocin stability at 1.5 h in both linear and cyclic structures by 58.2% and 79.1%, respectively. Substitution of three D-AAs into native cyclic oxytocin significantly increased peptide permeability across rat colonic tissue; this may be because D-AA substitution favourably altered the peptide’s secondary structure. This study is the first to show how the strategic design of peptide therapeutics could enable their delivery to the colon via the oral route.

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Holst, Pia Bachmann, Uffe Anthoni, Carsten Christophersen, Sine Larsen, Per Halfdan Nielsen, Ask Püschl, Kurt V. Mikkelsen, and Alexander Senning. "Cyclisations of Tryptophans. IV. Cyclisation of Nb-Acyl-L-Tryptophanamides." Acta Chemica Scandinavica 52 (1998): 683–93. http://dx.doi.org/10.3891/acta.chem.scand.52-0683.

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7

Joyce, Liam M., Anthony C. Willis, Christopher J. T. Hyland, and Stephen G. Pyne. "Gold- and Silver-Catalysed Cyclisation Reactions of β-Amino Allenes." Australian Journal of Chemistry 71, no. 9 (2018): 682. http://dx.doi.org/10.1071/ch18197.

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Herein we report the formation of pyrrolines and tetrahydropyridines from the cyclisation reactions of β-amino allenes by both AuI and AgI catalysts in yields ranging from 5 to 70 %. AuI catalysts favour a 5-endo-dig cyclisation before rapid rearrangement to the 5-exo-dig product, while AgI favours a 6-endo-trig cyclisation. We also report the first known Ag2O catalysed cyclisation reaction of an allene which occurred in good yield (61 %).

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Palík, Miroslav, Jozef Kožíšek, Peter Koóš, and Tibor Gracza. "Palladium-catalysed cyclisation of alkenols: Synthesis of oxaheterocycles as core intermediates of natural compounds." Beilstein Journal of Organic Chemistry 10 (September 3, 2014): 2077–86. http://dx.doi.org/10.3762/bjoc.10.216.

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The study of Pd-catalysed cyclisation reactions of alkenols using different catalytic systems is reported. These transformations affect the stereoselective construction of mono- and/or bicyclic oxaheterocyclic derivatives depending on a starting alkenol. The substrate scope and proposed mechanism of Pd-catalysed cyclisation reactions are also discussed. Moreover, the diastereoselective Pd-catalysed cyclisation of appropriate alkenols to tetrahydrofurans and subsequent cyclisation provided properly substituted 2,5-dioxabicyclo[2.2.1]heptane and 2,6-dioxabicyclo[3.2.1]octane, respectively. Such bicyclic ring subunits are found in many natural products including ocellenynes and aurovertines.

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Ferguson, Jayne L., Marie A. Squire, and Christopher M. Fitchett. "Photochemical and oxidative cyclisation of tetraphenylpyrroles." Organic & Biomolecular Chemistry 15, no. 44 (2017): 9293–96. http://dx.doi.org/10.1039/c7ob02537h.

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The cyclisation of tetraphenylpyrroles under complementary conditions allows controlled cyclisation giving products dependent on N-substitution, with both tandem rearrangement and halogenation being observed.

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Hayes, Heather C., Louis Y. P. Luk, and Yu-Hsuan Tsai. "Approaches for peptide and protein cyclisation." Organic & Biomolecular Chemistry 19, no. 18 (2021): 3983–4001. http://dx.doi.org/10.1039/d1ob00411e.

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Polypeptide cyclisation can enhance thermal stability, proteolytic resistance and membrane permeability. Cyclisation can be achieved by methods including chemical, enzyme and protein tag approaches. Each has strengths and limitations.

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Dissertations / Theses on the topic "Cyclisation"

1

Sukirthalingam, Sukanthini. "Palladium catalysed cyclisation processes." Thesis, Queen's University Belfast, 1990. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.335444.

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Chakraborty, Reena. "Cyclisation using bifunctional silanes." Thesis, University of Nottingham, 1991. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.335197.

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Wilmshurst, Martin Philip. "Fluoroalkyl radical cyclisation reactions." Thesis, University College London (University of London), 1998. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.286192.

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Bird, Andrew James. "Zirconium-mediated cyclisation reactions." Thesis, University of York, 1996. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.319766.

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Sykes, Bridget Maree. "Reductively triggered internal cyclisation reactions." Thesis, University of Auckland, 1994. http://hdl.handle.net/2292/1977.

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Reductively triggered internal cyclisation reactions have been investigated as a prodrug system for the hypoxia selective release of aromatic nitrogen mustards. The observed pseudo-first-order rate coefficients of cyclisation of several model 2-aminoaryl-acetamides and propanamides have been measured. Cyclisation was observed to be strongly influenced by stereochemistry, whereas electron withdrawal from the amine-bearing ring resulted in a comparatively modest slowing of the rate of cyclisation. Protonation of the leaving group appeared to increase the rate of cyclisation, while changes in 4-substitution on the leaving amine had little effect on this rate. The cyclisation of 2-(2-aminophenyl) alkanamides was found to be subject to general catalysis by acidic buffer components, and rate determining formation of the tetrahedral intermediate has been proposed. Ring closure reactions of several 2-hydroxylaminophenylalkanamides have been studied by γ-radiolysis. HPLC methods have been developed for the separation of reduction and cyclisation products. Reduction stoichiometry implicates the hydroxylamine as the predominant reduction product of radiolysis of the 2-nitrophenylalkanamide precursors, which varied in the nature of substitution of the nitrobenzyl ring, 4-substitution of the leaving aniline, and overall geometry. Cyclisation via the hydroxylamino was observed to be significantly faster than that of its amino counterparts, and was similarly influenced by changes in geometry. The hydroxylamine undergoes a base catalysed, oxygen dependent reaction under aerobic conditions. This reaction did not appear to be influenced by the geometry of the compound. Substitution of the hydroxylamine-bearing ring with a carboxamide group (CONHR σp = 0.36) lowered the pH at which hydroxylamino-amide cyclisation was slowest, compared with its unsubstituted counterpart. The reaction was found to be aided by electron-withdrawal from the leaving amine. Rate determining breakdown of the tetrahedral intermediate has been proposed. Preliminary investigations have been made on 2-nitrophenyl alkyl esters and a 2,6-dinitrophenylamide prodrug system. Rapid, reductively triggered release of coupled phenols and amines has been observed from the nitro-esters and -amides, respectively. In contrast to amino-amide and hydroxylamino-amide cyclisation, gem-dimethyl substitution did not facilitate reductive release from the nitro-ester. The inability to measure the rates of reductive release in radiolysis solutions suggests that these reactions occur significantly faster than hydroxylamino-amide ring closure. Molecular mechanics calculations have been undertaken to investigate relationships between the geometry of 2-aminoarylalkanamides, and rates of cyclisation. The distance between, and angle of approach of the nucleophilic and electrophilic centres in the calculated minimum-energy conformer did not display a correlation with cyclisation rates.
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6

Nilsson, Paul Andrew. "Radical cyclisation reactions of carbonyls." Thesis, Brunel University, 2002. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.270101.

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Pilling, Adam Wesley. "Site Isolation in Cyclisation Cascades." Thesis, University of Manchester, 2008. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.492762.

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This thesis concerns the exploitation of the site isolation concept in cascade sequences that facilitate rapid construction of complex polycyclic molecules. Site isolation is the anchoring of mutually destructive reagents onto solid supports to prevent their mutual deactivation.

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8

Nodes, William. "Novel intramolecular organocatalytic cyclisation reactions." Thesis, University of Reading, 2010. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.541961.

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9

Young, Adrian R. "Free radical cyclisation of imines." Thesis, Loughborough University, 1996. https://dspace.lboro.ac.uk/2134/15357.

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Introduction. The free radical cyclisation reaction onto an unsaturated bond is a well known synthetic pathway, where a wide range of cyclic compounds can be produced form acyclic starting materials. Up until recent years, free radical addition to multiple bonds other than carbon-carbon had been little studied. Nowadays there is much information available of radical addition to carbonyl, thiocarbonyl, nitrile and oxime ether (C=NOR) functional groups. However there has been surprisingly little detailed study of similar reactions involving imines (C=NR) or hydrazones (C=NNHR). Monocyclisation. In the early phase of the research, different types of imine were synthesised and subjected to the standard free radical cyclisation procedure (tributyl-tin hydride / AIBN, added by syringe pump to refluxing solvent) to determination of the regiochemistry of cyclisation onto imines and to assess the synthetic potential of the reaction. The results of this investigative study show that a variety of five and six-membered ring compounds can be synthesised in good yield. A similar study of hydrazones showed that fivemembered rings can be formed under the same reaction conditions. Tandem Reactions. In the next phase, the aim was to extend the methodology to produce more complex structures from acyclic starting materials. If a radical adds to the carbon atom of an imine, a nitrogen-centred (aminyl) radical is generated which can undergo subsequent addition to a suitably positioned double bond to yield a bicyclic amine. This type of reaction is known as tandem or cascade cyclisation. By this method, compounds could be synthesised which have similar structures to natural products. A range of suitably designed imines wct.5. prepared and underwent cyclisation, producing many different types of bicyclic amine in yields varying from moderate to good. The Synthesis of Natural Products. After the successful formation of key bicyclic structures, the third phase of the research aimed at the synthesis of one or more of target natural products. The synthetic strategy used in the tandem reactions outline above was. adapted for these purposes. However the synthesis of the desired compounds could not be achieved in the time, but progress towards their formation was achieved.

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Cecil, Alexander Richard Liam. "Asymmetric oxidative cyclisation of dienes." Thesis, University of Southampton, 2004. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.402065.

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Books on the topic "Cyclisation"

1

Tinkl, Michael. Stereocontrolled iron-mediated cyclisation routes to heterocycles. Norwich: University of East Anglia, 1994.

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Filik, Robert Paul. Synthesis of nitrogen containing heterocycles via radical cyclisation. [s.l.]: typescript, 2000.

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3

Idris, Ziad Moh'd. Synthesis and cyclisation of 2-benzamido-1-phenylcyclohexanols. Salford: University of Salford, 1988.

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4

Byrne, Maeve. The synthesis and cyclisation of 2-bromo-3-ethoxypropanones. Dublin: University College Dublin, 1998.

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5

Martin, Marie. The preparation and cyclisation of 5'- and 6'-Azachalcones. Dublin: University College Dublin, 1995.

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6

Y, Thebtaranonth, ed. Cyclization reactions. Boca Raton: CRC Press, 1994.

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7

Harmata, Michael. Advances in cycloaddition. Stamford, Conn: JAI Press, 1999.

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8

Cycloaddition reactions in organic synthesis. Oxford, England: Pergamon Press, 1990.

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Carruthers, W. Cycloaddition reactions in organic synthesis. Oxford: Pergamon, 1990.

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10

Lehn, J. M. Aspects de la chimie des compose s macrocycliques: Notes re dige es, augmente es et actualise es. Paris: InterEditions, 1991.

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Book chapters on the topic "Cyclisation"

1

Blanco-Urgoiti, Jaime, Gema Domínguez, Javier Pérez-Castells, Ligang Zhao, Xiyan Lu, Minsheng He, Aiwen Lei, et al. "Cyclisation Reactions." In Catalysts for Fine Chemical Synthesis, Volume 3, Metal Catalysed Carbon-Carbon Bond-Forming Reactions, 181–200. Chichester, UK: John Wiley & Sons, Ltd, 2005. http://dx.doi.org/10.1002/0470862017.ch10.

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Markó, István E. "Electroorganic Cyclisation of Oxygen-Containing Compounds." In Novel Trends in Electroorganic Synthesis, 7–10. Tokyo: Springer Japan, 1998. http://dx.doi.org/10.1007/978-4-431-65924-2_2.

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3

Louie, Janis. "N-Heterocyclic Carbene Complexes in Cyclisation Reactions." In Catalysis by Metal Complexes, 131–56. Dordrecht: Springer Netherlands, 2010. http://dx.doi.org/10.1007/978-90-481-2866-2_5.

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Gilbert, B. C., and C. W. McCleland. "Cyclisation of γ-Arylalkanols Via Aryl Radical-Cation and Alkoxyl Radical Intermediates." In Organic Free Radicals, 121–22. Berlin, Heidelberg: Springer Berlin Heidelberg, 1988. http://dx.doi.org/10.1007/978-3-642-73963-7_60.

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Fernández-García, Elisabet, José J. Ríos, Manuel Jarén-Galán, and Antonio Pérez-Gálvez. "Intramolecular Cyclisation as Structural Transformation of Carotenoids During Processing of Paprika (Capsicum annuumL.) and Paprika Oleoresins." In ACS Symposium Series, 207–17. Washington, DC: American Chemical Society, 2013. http://dx.doi.org/10.1021/bk-2013-1134.ch017.

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MacCorquodale, Finlay, and John C. Walton. "Unusual Transannular Radical Cyclisations." In Organic Free Radicals, 111–12. Berlin, Heidelberg: Springer Berlin Heidelberg, 1988. http://dx.doi.org/10.1007/978-3-642-73963-7_55.

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Rowan, S. J., P. A. Brady, and J. K. M. Sanders. "Selectivity in Thermodynamic Cyclisations of Cinchona Alkaloid Derivatives." In Molecular Recognition and Inclusion, 483–86. Dordrecht: Springer Netherlands, 1998. http://dx.doi.org/10.1007/978-94-011-5288-4_89.

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"CHAPITRE 2 Cyclisation." In Aspects de la chimie des composés macrocycliques, 15–38. EDP Sciences, 1991. http://dx.doi.org/10.1051/978-2-7598-0265-4.c006.

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9

Ward, Robert S. "Cyclisation versus polymerisation." In Bifunctional Compounds. Oxford University Press, 1994. http://dx.doi.org/10.1093/hesc/9780198558088.003.0011.

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This chapter reviews the competition between cyclization and polymerization and states that this can be influenced in several ways, such as through varying the concentration of the solution. It demonstrates a method that can be used to promote cyclization at the expense of polymerization, namely to carry out the reaction in dilute solution so that the probability of an intermolecular reaction taking place is reduced. It also talks about the entropy factor, a measure of the probability of the two ends of the chain coming into contact with one another. The chapter explains that the enthalpy factor can be correlated with the stability of the ring being produced and is most favourable for six-membered rings. It concludes that five- and six-membered rings are obtained easily by cyclization, while three- or four-membered rings are difficult to obtain through this method. The chapter goes on to discuss the preparation of non-aromatic carbocyclic compounds and non-aromatic heterocyclic compounds, as well as the polymerization of bifunctional compounds.

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"CHAPITRE 3 Méthodes de cyclisation." In Aspects de la chimie des composés macrocycliques, 39–180. EDP Sciences, 1991. http://dx.doi.org/10.1051/978-2-7598-0265-4.c007.

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Conference papers on the topic "Cyclisation"

1

Stadelmann, Sacha, Stéphane Mayor, Roger Marti, and Marc Mathieu. "Depsipeptide cyclisation: Lactonization vs. Lactamisation." In 35th European Peptide Symposium. Prompt Scientific Publishing, 2018. http://dx.doi.org/10.17952/35eps.2018.166.

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Arrasate, Sonia, Esther Lete, Nuria Sotomayor, and Media Abdullah. "Stereoselective Synthesis of Thiaerythrinanes via Parham Cyclisation." In The 11th International Electronic Conference on Synthetic Organic Chemistry. Basel, Switzerland: MDPI, 2007. http://dx.doi.org/10.3390/ecsoc-11-01318.

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Kohler, Armin, and Bernd Bertsche. "Cyclisation of Safety Diagnoses: Influence on the Evaluation of Fault Metrics." In 2021 Annual Reliability and Maintainability Symposium (RAMS). IEEE, 2021. http://dx.doi.org/10.1109/rams48097.2021.9605716.

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Amaral, André F. C., Guilherme D. R. Matos, Inês S. Resck, and Elaine R. Maia. "Stereochemical and 13C NMR study in order to characterize intermediates obtained by cyclisation of diisoxazoledilactone." In 14th Brazilian Meeting on Organic Synthesis. São Paulo: Editora Edgard Blücher, 2013. http://dx.doi.org/10.5151/chempro-14bmos-r0322-1.

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Raposo, M., Ana Sampaio, and G. Kirsch. "Synthesis of Arylamino-thieno-oxobutanamides and Reactivity Studies on the Cyclisation with the Lawesson's Reagent." In The 8th International Electronic Conference on Synthetic Organic Chemistry. Basel, Switzerland: MDPI, 2004. http://dx.doi.org/10.3390/ecsoc-8-01947.

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