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Silica-supported ceric ammonium nitrate (CAN): a simple, mild and solid-supported reagent for quickest oxidative aromatization of Hantzsch 1,4-dihydropyridines

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Abstract

An efficient and environmentally benign methodology for the oxidative aromatization of 1,4-dihydropyridines to their corresponding pyridine derivatives is developed. The oxidative aromatization of 1,4-dihydropyridines was explored using silica-supported ceric ammonium nitrate as catalyst in CH3CN with or without sonication at room temperature. This supported catalyst acts as a more efficient oxidising reagent and offers several advantages over other reported reagents in terms of reaction time and yields. The supported reagent is found to be more efficient and selective when compared with its unsupported form. The Belousov–Zhabotinskii reaction was not observed in present reaction. The dealkylation observed in case of 4-n-alkyl/n-alkenyl with other oxidising agents is also not observed in the present case.

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Acknowledgements

Kulbir Kadyan thanks UGC for providing junior research fellowship (JRF).

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Authors and Affiliations

  1. Department of Chemistry, Kurukshetra University, Kurukshetra, 136119, Haryana, India

    Parvin Kumar, Kulbir Kadyan, Meenakshi Duhan & Sohan Lal

  2. Department of Chemistry, K. M. Government College, Narwana, 126116, Haryana, India

    Jayant Sindhu

  3. Chemistry Department, Mewat Engineering College, Palla, Nuh, 122107, Haryana, India

    Khalid Hussain

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  1. Parvin Kumar
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  2. Kulbir Kadyan
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  3. Meenakshi Duhan
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Correspondence to Parvin Kumar.

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Kumar, P., Kadyan, K., Duhan, M. et al. Silica-supported ceric ammonium nitrate (CAN): a simple, mild and solid-supported reagent for quickest oxidative aromatization of Hantzsch 1,4-dihydropyridines. Chem. Pap. 73, 1153–1162 (2019). https://doi.org/10.1007/s11696-018-0666-5

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