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Guanidinium-based sulfonic acid: an efficient Brønsted acid organocatalyst for the synthesis of fused polycyclic dihydropyridines in water

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Abstract

An efficient and eco-friendly protocol for the synthesis of polycyclic dihydropyridine scaffolds has been developed from readily accessible 4-hydroxycoumarin, aldehydes, and ammonium acetate in the presence of guanidinium-based sulfonic acid as a Brønsted acid organocatalyst. This method provides several advantages, such as simple work-up procedure, environmentally benign, recyclable catalyst, and high yields. In addition, water was chosen as a green solvent.

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Fig. 1
Scheme 1
Fig. 2
Scheme 2

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Notes

  1. To a mixture of 4-hydroxycoumarin 1 (0.16 g, 1.00 mmol), an aldehyde 2 (0.50 mmol) and ammonium acetate 3 (0.15 g, 2.00 mmol) was added guanidinium-based sulfonic acid (0.01 g, 5 mol%) in water (5 mL). The mixture was refluxed for 5 h. After completion of the reaction, as indicated by TLC (EtOAc:n-hexane, 1:1), the reaction mixture was cooled to room temperature. Then, the precipitated product was filtered and washed with water to afford the pure product 4a–l.

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Acknowledgments

We gratefully acknowledge financial support of the Iran National Elites Foundation (INEF) and the Research Council of Shahid Beheshti University.

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Authors and Affiliations

  1. Faculty of Chemistry, Shahid Beheshti University, G. C., P. O. Box 19396-4716, Tehran, Iran

    Ahmad Shaabani, Shabnam Shaabani, Mozhdeh Seyyedhamzeh, Mona Hamidzad Sangachin & Fatemeh Hajishaabanha

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  1. Ahmad Shaabani
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  2. Shabnam Shaabani
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Correspondence to Ahmad Shaabani.

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Shaabani, A., Shaabani, S., Seyyedhamzeh, M. et al. Guanidinium-based sulfonic acid: an efficient Brønsted acid organocatalyst for the synthesis of fused polycyclic dihydropyridines in water. Res Chem Intermed 42, 7247–7256 (2016). https://doi.org/10.1007/s11164-016-2533-8

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  • DOI: https://doi.org/10.1007/s11164-016-2533-8

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