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The clean and mild synthesis, crystal structure, and intra-molecular hydrogen bond study of substituted new 4,8-dihydropyrano[3,2-b]-pyrans containing chlorokojic acid moiety

  • Khadijeh Ojaghi Aghbash
  • Nader Noroozi PesyanEmail author
  • Ghasem Marandi
  • Necmi Dege
  • Ertan Şahin
Article
  • 10 Downloads

Abstract

A safe, green and convenient process was developed for the synthesis of a novel group of 4,8-dihydropyrano[3,2-b]-pyrans by dialkyl acetylenedicarboxylates and alkyl isocyanides being trapped by chlorokojic acid in good to excellent yields at ambient temperature. Characterization of all structures was carried out by FT-IR and 1H and 13C NMR spectrometers, and two compounds were analyzed using X-ray diffraction technique. Crystal structures showed an intramolecular hydrogen bond and stacking of the dimeric (RS) molecules with the unit cell along the a-axis.

Keywords

Chlorokojic acid Isocyanides Acetylene esters Nucleophilic addition 4H-Pyran 4,8-Dihydropyrano[3,2-b]-pyran Intramolecular H bond Inversion dimers 

Notes

Acknowledgements

For all the crystal structures in this research, the reported crystallography data was published by the Cambridge Crystallographic Data Center (CCDC) as a supplemental publication [nos. CCDC-1874431 (3a) and 1874430 (3d)]. These data copies can be obtained free on application to the CCDC, UK, Cambridge CB2 1EZ, 12 Union Road; FAX: (+44) 1223 336033, or emailing data_request@ccdc.cam.ac.uk or by online via www.ccdc.cam.ac.uk/data_request/cif. Also, we thank the Research Council of the Urmia University that supported this work.

Supplementary material

11164_2019_3848_MOESM1_ESM.pdf (1.9 mb)
The 13C, 1H NMR, and FT-IR spectroscopic data for compounds 3a3f and X-ray data for 3a and 3d are available (PDF 1965 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 Physics, Faculty of Art and SciencesOndokuz Mayıs UniversitySamsunTurkey
  3. 3.Department of Chemistry, Faculty of ScienceAtatürk UniversityErzurumTurkey

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