Monatshefte für Chemie - Chemical Monthly

, Volume 149, Issue 11, pp 2059–2067 | Cite as

The clean synthesis and confirmatory structural characterization of new 2-amino-4,8-dihydropyrano[3,2-b]pyran-3-cyano based on Kojic acid

  • Khadijeh Ojaghi Aghbash
  • Nader Noroozi PesyanEmail author
  • Behrouz Notash
Original Paper


A valuable and clean method was developed for the synthesis of the group of different novel 2-amino-4,8-dihydropyrano[3,2-b]pyran-3-carbonitriles containing a 2-aminopyran moiety by using of azido kojic acid and various 2-arylidinemalononitriles in the presence of NH4Cl as a catalyst in a green solvent (ethanol) with excellent yields. All structures were analyzed by FT-IR, 1H, 13C NMR spectroscopy, and representatively, one compound was analyzed by X-ray crystallography technique. Crystallographic analyses indicated that of this compound a dimer formed via two weak intermolecular hydrogen bonds with d(N···O) distances of 2.927 Å and made a 14-membered ring with centrosymmetric (Ci) form.

Graphical abstract


Kojic acid Azido kojic acid Michael addition Pyran 2-Amino-4,8-dihydropyrano[3,2-b]pyran-3-carbonitrile 



We thank the Urmia University Research Council for supporting this work.

Supplementary material

706_2018_2254_MOESM1_ESM.pdf (3.3 mb)
Supplementary material 1 (PDF 3385 kb)


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Copyright information

© Springer-Verlag GmbH Austria, part of Springer Nature 2018

Authors and Affiliations

  1. 1.Department of Organic Chemistry, Faculty of ChemistryUrmia UniversityUrmiaIran
  2. 2.Department of Chemistry, Faculty of ScienceShahid Beheshti UniversityTehranIran

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