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    One-Pot Synthesis of Fluorescent 2,5-Dihydro-1,2,3-triazine Derivatives from a Cascade Rearrangement Sequence in the Reactions of 1,2,3-Triazolium-1-aminide 1,3-Dipoles with Propiolate Esters


    Butler, Richard N. and Fahy, Aoife and Fox, Anthony and Stephens, John C. and McArdle, P. and Cunningham, D. and Ryder, A. (2006) One-Pot Synthesis of Fluorescent 2,5-Dihydro-1,2,3-triazine Derivatives from a Cascade Rearrangement Sequence in the Reactions of 1,2,3-Triazolium-1-aminide 1,3-Dipoles with Propiolate Esters. Journal of Organic Chemistry, 71 (15). pp. 5679-5687. ISSN 0022-3263

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    Abstract

    The reactions of 1,2,3-triazolium-1-aminides 1 (readily available from benzil bishydrazones) with propiolate esters leads to fluorescent 2,5-dihydro-1,2,3-triazine derivatives 2, 3 in one pot. These synthetic reactions can be carried out in acetone, in water, or under solvent-free conditions. The reactions involve a Huisgen cycloaddition followed by a sequence of rearrangements. The final ring-expansion step was blocked by linking a six-methylene hydrocarbon chain between the prospective 1,2,3-triazine C-4 and C-6 atoms, using substrate 8 which gave the fused tricyclic azapropellane product 9 exclusively. X-ray crystal structures were determined for two 2,5-dihydro-1,2,3-triazine derivatives and for compound 9. The UV absorption of the 1,2,3-triazine derivatives showed a dual absorption at ca. 310 and ca. 390 nm with fluorescent emission at ca. 480 and 528 nm (for excitation at 317 nm). The significant Stokes shift of ca. 200 nm shows the potential for biological fluorescent labeling experiments.

    Item Type: Article
    Keywords: One-Pot Synthesis; Fluorescent 2,5-Dihydro-1,2,3-triazine Derivatives; Cascade Rearrangement Sequence; 1,2,3-Triazolium-1-aminide 1,3-Dipoles; Propiolate Esters;
    Academic Unit: Faculty of Science and Engineering > Chemistry
    Item ID: 7819
    Identification Number: https://doi.org/10.1021/jo060752x
    Depositing User: Dr John Stephens
    Date Deposited: 27 Jan 2017 15:29
    Journal or Publication Title: Journal of Organic Chemistry
    Publisher: American Chemical Society
    Refereed: Yes
    Funders: Irish Research Council for Science Engineering and Technology (IRCSET), Science Foundation Ireland (SFI)
    URI:

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