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Synthesis of novel 3-[(1-glycosyl-1H-1,2,3-triazol-4-yl)- methylamino]ket-2-en-1-ones

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Chemistry of Heterocyclic Compounds Aims and scope

Nine 3-[(1-β-D-ribofuranosyl- and 3-[(1-β-D-glucopyranosyl-1H-1,2,3-triazol-4-yl)methylamino]ket-2-en-1-ones have been synthesized by copper-catalyzed azide–alkyne cycloaddition (CuAAC) reaction between propargylamine derivatives and 1-azido-2,3,5-tri-O-benzoylβ-D-ribofuranose or 2,3,4,6-tetra-O-acetyl-1-azido-β-D-glucopyranose, followed by deprotection of the resulting tri-O-benzoyl- or tetraO-acetyl-1-β-D-glycosyltriazoles in good yields. The precursor propargylamine derivatives were synthesized by Sonogashira reaction of substituted acetylenes and benzoyl chloride followed by Michael-type addition of propargylamine to the resulting substituted alkynes in good yields. The precursor azido sugars, 1-azido-2,3,5-tri-O-benzoyl-β-D-ribofuranose and 2,3,4,6-tetra-O-acetyl-1-azido-β-D-glucopyranose, were synthesized by azidation of 1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose and β-D-glucopyranose pentacetate, respectively, with azidotrimethylsilane in the presence of tin(IV) chloride. All products were unambiguously characterized on the basis of the spectral data analysis.

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We are grateful to University of Delhi for providing financial support under DU-DST Purse grant to strengthen research and development. We are also thankful to CIF-USIC, University of Delhi for providing the NMR spectral and HRMS recording facilities.

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Authors and Affiliations

  1. Bioorganic Laboratory, Department of Chemistry, University of Delhi, Delhi, 110 007, India

    Banty Kumar, Jyotirmoy Maity, Amit Kumar, Vinod Khatri, Bhawani Shankar & Ashok K. Prasad

  2. Rajdhani College, Department of Chemistry, University of Delhi, Delhi, 110 007, India

    Banty Kumar

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  1. Banty Kumar
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  2. Jyotirmoy Maity
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  3. Amit Kumar
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  4. Vinod Khatri
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  5. Bhawani Shankar
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  6. Ashok K. Prasad
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Correspondence to Ashok K. Prasad.

Additional information

Supplementary information file containing 1H and 13C NMR data of all synthesized compounds is available at the journal website at http://link.springer.com/journal/10593.

Published in Khimiya Geterotsiklicheskikh Soedinenii, 2018, 54(3), 362–368

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Kumar, B., Maity, J., Kumar, A. et al. Synthesis of novel 3-[(1-glycosyl-1H-1,2,3-triazol-4-yl)- methylamino]ket-2-en-1-ones. Chem Heterocycl Comp 54, 362–368 (2018). https://doi.org/10.1007/s10593-018-2274-2

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  • DOI: https://doi.org/10.1007/s10593-018-2274-2

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