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Molecular Diversity

, Volume 21, Issue 1, pp 247–255 | Cite as

A facile, efficient, and sustainable chitosan/CaHAp catalyst and one-pot synthesis of novel 2,6-diamino-pyran-3,5-dicarbonitriles

  • Suresh Maddila
  • Kranthi Kumar Gangu
  • Surya Narayana Maddila
  • Sreekantha B. JonnalagaddaEmail author
Short Communication

Abstract

A simple and versatile one-pot three-component synthetic protocol is devised for heterocycles, viz. 2,6-diamino-4-substituted-4H-pyran-3,5-dicarbonitrile derivatives, in short reaction times (\(\approx \)30 min) at room temperature using ethanol as a solvent. This method involves the three-component reaction of malononitrile, substituted aldehydes, and cyanoacetamide catalyzed by chitosan-doped calcium hydroxyapatites (CS/CaHAps) giving good to excellent yields (86–96%). Twelve new pyran derivatives (4al) were synthesized and their structures were established and confirmed by different spectroscopic methods (\(^{1}\)H NMR, \(^{13}\)C NMR, \(^{15}\)N NMR, and HRMS). The heterogeneous catalyst, CS/CaHAp, was characterized by various instrumental techniques including XRD, TEM, SEM, and FT-IR and TGA spectroscopies. The catalyst was easily separable and reusable for up to six runs without any apparent loss of activity. The reported protocol has many benefits, such as ease of preparation, use of a green solvent, reduced reaction times, excellent product yields, and operational simplicity.

Graphical Abstract

Keywords

Green synthesis Pyrans Multicomponent reactions MCRs Heterogeneous catalyst Chitosan Hydroxyapatite Recyclability 

Notes

Acknowledgements

The authors are thankful to the National Research Foundation (NRF) of South Africa and University of KwaZulu-Natal, Durban, for financial support and research facilities.

Supplementary material

11030_2016_9708_MOESM1_ESM.doc (2.6 mb)
Supplementary material 1 (doc 2667 KB)

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Copyright information

© Springer International Publishing Switzerland 2016

Authors and Affiliations

  1. 1.School of Chemistry & PhysicsUniversity of KwaZulu-NatalDurbanSouth Africa

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