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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

  • Khadijeh Ojaghi Aghbash
  • Nader Noroozi PesyanEmail author
  • Ertan Şahin
Article
  • 22 Downloads

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.

Keywords

4H-pyrans 2-Amino-6-(azidomethyl)-4,8-dihydropyrano[3,2-b]pyran-3-carbonitrile Azide-alkyne 1,3-dipolar cycloaddition Click reaction Copper catalysis 1,2,3-Triazoles Dimeric form Co-crystal 

Notes

Acknowledgement

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

Supplementary material

11164_2018_3723_MOESM1_ESM.pdf (4.6 mb)
Supporting Information Spectroscopic data including FT IR, 1H and 13C NMR spectra of 4a4m and also crystallographic data for 4j are available. (PDF 4692 kb)

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Copyright information

© Springer Nature B.V. 2019

Authors and Affiliations

  1. 1.Department of Organic Chemistry, Faculty of ChemistryUrmia UniversityUrmiaIran
  2. 2.Department of Chemistry, Faculty of ScienceAtatürk UniversityErzurumTurkey

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