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Cu(I)-catalyzed alkyne–azide ‘click’ cycloaddition (CuAAC): a clean, efficient, and mild synthesis of new 1,4-disubstituted 1H-1,2,3-triazole-linked 2-amino-4,8-dihydropyrano[3,2-b]pyran-3-carbonitrile–crystal structure

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Abstract

Cu(I)-catalyzed alkyne–azide ‘click’ cycloaddition (CuAAC) is an important ‘‘click chemistry’’ reaction that is widely known in materials science, chemical biology, and pharmaceutical chemistry. The CuAAC reaction of terminal alkynes affords an efficient and mild production of triazolic 1,4-disubstituted compounds. In this work, a green and valuable method was introduced for the synthesis of the category of different new 1,4-disubstituted 1,2,3-triazole swapped with a 2-amino-4,8-dihydropyrano[3,2-b]pyran-3-cyano moiety. These triazolic derivatives were produced by treatment of various 2-amino-6-(azidomethyl)-4,8-dihydropyrano[3,2-b]pyran-3-carbonitriles with phenylacetylene in the presence of CuI as a catalyst with excellent yields (because CuAAC is selective to 1,4-disubstituted triazole derivatives) in a green solvent (ethanol/water). All structures were evaluated by 13C, 1H NMR, and FT-IR spectroscopy and a compound was analyzed by crystallography (X-ray) technique.

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Acknowledgement

We much thanks to the Urmia University research council for supporting this research.

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Authors and Affiliations

  1. Department of Organic Chemistry, Faculty of Chemistry, Urmia University, Urmia, 57159, Iran

    Khadijeh Ojaghi Aghbash & Nader Noroozi Pesyan

  2. Department of Chemistry, Faculty of Science, Atatürk University, 25240, Erzurum, Turkey

    Ertan Şahin

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  1. Khadijeh Ojaghi Aghbash
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Correspondence to Nader Noroozi Pesyan.

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Spectroscopic data including FT IR, 1H and 13C NMR spectra of 4a–4m and also crystallographic data for 4j are available. (PDF 4692 kb)

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Ojaghi Aghbash, K., Noroozi Pesyan, N. & Şahin, E. Cu(I)-catalyzed alkyne–azide ‘click’ cycloaddition (CuAAC): a clean, efficient, and mild synthesis of new 1,4-disubstituted 1H-1,2,3-triazole-linked 2-amino-4,8-dihydropyrano[3,2-b]pyran-3-carbonitrile–crystal structure. Res Chem Intermed 45, 2079–2094 (2019). https://doi.org/10.1007/s11164-018-03723-x

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