Now showing items 34-53 of 57

  • Regioselective Substituent Effects upon the Synthesis of Dipyrrins from 2-Formyl Pyrroles 

    Regioselective Substituent Effects upon the Synthesis of Dipyrrins from 2-Formyl Pyrroles. Beh, M.H.R.; Figliola, C.; Lund, K-l. A.R.; Kajetanowicz, A.K.; Johnsen, A.E.; Aronitz, E.M.; Thompson, A. Can. J. Chem. 2018, 96, 779-784, special issue to honour Dalhousie’s 200th anniversary (NSERC). https://doi.org/10.1139/cjc-2017-0662
    The synthesis of symmetric α-free meso-H-dipyrrin hydrobromides from 5-H-2-formyl pyrroles was investigated. The self-condensation produces regioisomeric dipyrrins through the adoption of two mechanistic pathways. The key ...
  • Robust Synthesis of F-BODIPYs 

    Publisher's version: Beh, Michael; Douglas, Katherine; House, Kelsey; Murphy, Alexandra; Sinclair, Jackson; and Thompson, Alison. Robust Synthesis of F-BODIPYs. Org. Biomol. Chem. 2016, 14, 11473-11479. DOI: 10.1039/c6ob02238c
    F-BODIPYs are widely used in applications that rely upon their highly tunable optical properties. A protocol is established for the high-yielding synthesis of F-BODIPYs involving non-anhydrous reagents and not requiring ...
  • Scope and limitations in sulfur ylide mediated catalytic asymmetric aziridination of imines: use of phenyldiazomethane, diazoesters and diazoacetamides 

    Aggarwal, VK, M. Ferrara, CJ O'Brien, A. Thompson, et al. 2001. "Scope and limitations in sulfur ylide mediated catalytic asymmetric aziridination of imines: use of phenyldiazomethane, diazoesters and diazoacetamides." Journal of the Chemical Society-Perkin Transactions 1: 1635-1643.
    No abstract available.
  • Self-assembly of novel trimers using dipyrromethene ligands 

    Thompson, A., SJ Rettig, and D. Dolphin. 1999. "Self-assembly of novel trimers using dipyrromethene ligands." Chemical Communications: 631-632.
    Ligands comprising two dipyrromethene units linked at the beta-position have been used to prepare trimeric complexes with Zn-II and Co-II; the structure of the Zn-II complex is confirmed by X-ray analysis.
  • Step-wise synthetic approach is necessary to access g-conjugates of folate: folate-conjugated prodigiosenes 

    Despite the vast literature that describes reacting folic acid with a pharmacophore, this route is ineffective in providing the correct regioisomer of the resulting conjugate. We herein present a step-wise route to the ...
  • Synthesis and Anticancer Activity of Prodigiosenes bearing C-Ring Esters and Amides 

    Published version: Lund, K., Figliola, C., Kajetanowicz, A. & Thompson, A. (2017) Synthesis and Anticancer Activity of Prodigiosenes bearing C-Ring Esters and Amides, RSC Advances, 50 (7), 18617. doi: 10.1039/c7ra01628j
  • Synthesis and Antimalarial Activity of Prodigiosenes 

    Marchal, E., Smithen, D. A., Uddin, M. I., Robertson, A. W., Jakeman, D. L., Mollard, V., ... & Thompson, A. (2014). Synthesis and antimalarial activity of prodigiosenes. Organic & biomolecular chemistry, 12(24), 4132-4142. DOI:b10.1039/C3OB42548G
    Several analogues of the natural compound prodigiosin with modified A- and C-rings were synthesised as were some of their tin, cobalt, boron and zinc complexes. The antimalarial activity of these prodigiosenes was evaluated ...
  • Synthesis and biological evaluation of prodigiosene conjugates of porphyrin, estrone and 4-hydroxytamoxifen 

    Hawco, C. L., Marchal, E., Uddin, M. I., Baker, A. E., Corkery, D. P., Dellaire, G., & Thompson, A. (2013). Synthesis and biological evaluation of prodigiosene conjugates of porphyrin, estrone and 4-hydroxytamoxifen. Bioorganic & medicinal chemistry, 21(19), 5995-6002. DOI: 10.1016/j.bmc.2013.07.042}
    To generate the first series of prodigiosene conjugates, the tripyrrolic skeleton was appended to estrone, tamoxifen and porphyrin frameworks by way of ester linkers and various hydrocarbon chain lengths. The ability of ...
  • Synthesis and characterisation of the unsubstituted dipyrrin and 4,4-dichloro-4-bora-3a,4a-diaza-s-indacene: improved synthesis and functionalisation of the simplest BODIPY framework 

    Groves, Brandon R., Sarah M. Crawford, Travis Lundrigan, Cherif F. Matta, et al. 2013. "Synthesis and characterisation of the unsubstituted dipyrrin and 4,4-dichloro-4-bora-3a,4a-diaza-s-indacene: improved synthesis and functionalisation of the simplest BODIPY framework." Chemical Communications 49(8): 816-818.
    An improved and scalable synthesis of the unsubstituted 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene framework facilitates access to the previously unreported parent dipyrrin HCl salt, as well as 4,4-dichloro-4-bora-3a,4a- ...
  • Synthesis and Characterization of Pyrrolyldipyrrin F-BODIPYs 

    Greening, S. M., Robertson, K. N., & Thompson, A. (2018). Synthesis and characterization of pyrrolyldipyrrin F-BODIPYs. Photochemical & Photobiological Sciences, 17(1), 89-98. DOIO: 10.1039/C7PP00341B
    A series of synthetic analogs of the tripyrrolic natural product prodigiosin were complexed with boron trifluoride to generate the corresponding F-BODIPYs. The maximum wavelengths of absorption and emission of the ...
  • Synthesis and Photobiological Activity of Ru(II) Dyads Derived from Pyrrole-2-Carboxylate Thionoesters 

    Deborah A. Smithen, Huimin Yin, Michael H. R. Beh, Marc Hetu, T. Stanley Cameron, Sherri A. McFarland,*and Alison Thompson. (2017). Inorganic Chemistry, 56, 4121-4132. DOI: 10.1021/acs.inorgchem.7b00072
  • Synthesis and reactivity of 2-thionoester pyrroles: a route to 2-formyl pyrroles 

    Kim, Min Joon; Gaube, Sophie M.; Beh, Michael H. R.; Smith, Craig D.; Thompson, Alison. (2019). RSC Advances.
    2-Functionalised pyrroles exhibit considerable synthetic utility. Herein, the synthesis and reactivity of 2-thionoester (-C(S)OR) pyrroles is reported. 2-Thionoester pyrroles were synthesized using a Knorr-type approach ...
  • Synthesis and Reactivity of Aza-Dipyrrin Alkali Metal Salts 

    Synthesis and Reactivity of Aza-Dipyrrin Alkali Metal Salts. Diaz-Rodriguez, R.M.; Robertson, K.N.; Thompson, A. Chem. Commun. 2018, accepted, CC-COM-09-2018-007101.R1 (NSERC) DOI: 10.1039/C8CC07101B
    We report the lithium, sodium and potassium salts of aza-dipyrrins and detail their use as anionic aza-dipyrrinato ligand sources in complexation. Of the three types of alkali salts studied, those of lithium are found to ...
  • Synthesis of dipyrrins bearing chirality adjacent to the conjugated skeleton - Electron-poor pyrroles exhibit dramatically reduced nucleophilicity 

    Beshara, Cory S., Beth M. Pearce, and Alison Thompson. 2008. "Synthesis of dipyrrins bearing chirality adjacent to the conjugated skeleton - Electron-poor pyrroles exhibit dramatically reduced nucleophilicity." Canadian Journal of Chemistry-Revue Canadienne De Chimie 86(10): 951-957.
    With the aim of furthering our investigations into the asymmetric complexation of dipyrrinato ligands, a dipyrrin bearing a stereogenic centre directly adjacent to the conjugated skeleton was synthesized. The electron- ...
  • Synthesis of heteroleptic pyrrolide/bipyridyl complexes of ruthenium(II) 

    Lundrigan, Travis, Carla L. M. Jackson, Md Imam Uddin, Lloyd A. Tucker, et al. 2012. "Synthesis of heteroleptic pyrrolide/bipyridyl complexes of ruthenium(II)." Canadian Journal of Chemistry-Revue Canadienne De Chimie 90(8): 693-700.
    The synthesis and characterization of the first heteroleptic pyrrolide/2,2'-bipyridyl complexes of ruthenium(II) are reported. Pyrroles substituted at the 2-position with X = O functionality react with Ru(bipy)(2)Cl-2.2H(2)O ...
  • Synthesis of natural products containing the pyrrolic ring 

    Young, Ian S., Paul D. Thornton, and Alison Thompson. 2010. "Synthesis of natural products containing the pyrrolic ring." Natural Product Reports 27(12): 1801-1839.
    This review provides an overview of the synthetic chemistry that has been utilised to prepare natural products containing a pyrrolic ring.
  • Synthesis of Prodigiosene-Estrogen Conjugates: optimization of protecting group strategies and anticancer properties 

    Marchal, E., Uddin, M. I., Hawco, C. L., & Thompson, A. (2015). Synthesis of prodigiosene–estrogen conjugates: optimization of protecting group strategies and anticancer properties. Canadian Journal of Chemistry, 93(5), 526-535. https://doi.org/10.1139/cjc-2014-0516
    The tripyrrolic prodigiosene skeleton was conjugated to several estrogen ligands. The conjugation was achieved via an ester linker that proved to be unusually sensitive to hydrolysis during synthesis. This work describes ...
  • Synthesis of sulfenyl dipyrroles via reaction of a-free pyrroles with thionyl chloride 

    Beh, Michael H. R.; Smith, Craig D.; Robertson, Katherine N.; and Thompson, Alison. (2020). Synthesis of sulfenyl dipyrroles via reaction of a-free pyrroles with thionyl chloride. Canadian Journal of Chemistry,
  • Synthesis of symmetric meso-H dipyrrin hydrobromides from 2-formyl pyrroles 

    Lund, K. L. A., & Thompson, A. (2014). Synthesis of Symmetric meso-H-Dipyrrin Hydrobromides from 2-Formylpyrroles. Synlett, 25(08), 1142-1144. DOI: 10.1055/s-0033-1341066
    The reaction of 2-formyl pyrroles in acidic methanol gives the corresponding symmetric, meso-H 4,6-dipyrrin hydrobromides. This convenient strategy involves initial deformylation under the acidic conditions, followed by ...
  • Synthesis, properties and reactivity of BCl2 aza-BODIPY complexes and salts of the aza-dipyrrinato scaffold 

    Diaz-Rodriguez, R. M., Burke, L., Robertson, K. N., & Thompson, A. (2020). Synthesis, properties and reactivity of BCl 2 aza-BODIPY complexes and salts of the aza-dipyrrinato scaffold. Organic & Biomolecular Chemistry, 18(11), 2139-2147.
    The synthesis and characterisation of the BCl2-chelated complexes of both archetypal aza-dipyrrin sub- types are presented. A stepwise halogen exchange, leading to a mixed-halide Cl–B–F intermediate, is implicated in the ...