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

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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 (4a–l) 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.

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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.

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  1. School of Chemistry & Physics, University of KwaZulu-Natal, Westville Campus, Chiltern Hills, Durban, 4000, South Africa

    Suresh Maddila, Kranthi Kumar Gangu, Surya Narayana Maddila & Sreekantha B. Jonnalagadda

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  1. Suresh Maddila
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  2. Kranthi Kumar Gangu
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  3. Surya Narayana Maddila
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  4. Sreekantha B. Jonnalagadda
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Correspondence to Sreekantha B. Jonnalagadda.

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Maddila, S., Gangu, K.K., Maddila, S.N. et al. A facile, efficient, and sustainable chitosan/CaHAp catalyst and one-pot synthesis of novel 2,6-diamino-pyran-3,5-dicarbonitriles. Mol Divers 21, 247–255 (2017). https://doi.org/10.1007/s11030-016-9708-5

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