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2-Hydroxyethylammonium acetate: an efficient and reusable homogeneous catalyst for the synthesis of Hantzsch 1,4-dihydropyridines

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Abstract

2-Hydroxyethylammonium acetate ionic liquid was found to be an excellent catalyst for the one-pot synthesis of 1,4-dihydropyridine derivatives via Hantzsch reaction of ethyl acetoacetate or acetoacetanilide, ammonium acetate, and various aromatic aldehydes. The combinatorial syntheses were achieved for the first time using 2-hydroxyethylammonium acetate ionic liquid as a homogeneous catalyst. The catalyst was active for the Hantzsch reaction in alcohol at reflux. The products were isolated in good yields (78–93 %). The resulting substituted dihydropyridines were characterized and confirmed by1H NMR spectral data. The catalyst offers simple means for recovery and the isolated catalyst was reused for three rounds for the synthesis without significant loss of catalytic activity. For all the other reactions carried out with the recycled catalyst, results were similar to that with the fresh catalyst.

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Acknowledgments

We are grateful to the Science and Technology Foundation of Shanghai Institute of Technology for financial support.

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Authors and Affiliations

  1. School of Chemical and Environmental Engineering, Shanghai Institute of Technology, 100 Haiquan Road, Shanghai, 201418, People’s Republic of China

    Li-Qin Kang, Zhi-Jun Cao & Ze-Jun Lei

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  1. Li-Qin Kang
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  2. Zhi-Jun Cao
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  3. Ze-Jun Lei
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Correspondence to Li-Qin Kang.

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Kang, LQ., Cao, ZJ. & Lei, ZJ. 2-Hydroxyethylammonium acetate: an efficient and reusable homogeneous catalyst for the synthesis of Hantzsch 1,4-dihydropyridines. Monatsh Chem 147, 1125–1128 (2016). https://doi.org/10.1007/s00706-015-1587-4

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  • DOI: https://doi.org/10.1007/s00706-015-1587-4

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