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Reusable silica-bonded S-sulfonic acid catalyst for three-component synthesis of 2-amino-5-oxo-5,6,7,8-tetrahydro-4H-chromenes and 2-amino-4H-pyrans in aqueous ethanol

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Abstract

Silica-bonded S-sulfonic acid (SBSSA)-catalyzed, facile, one-pot, three-component coupling of 5,5-dimethyl-1,3-cyclohexanedione (dimedone) or 5,5-dimethyl-1,3-cyclohexanedione, aromatic aldehydes, and malononitrile at reflux temperature is described for preparation of 2-amino-5-oxo-5,6,7,8-tetrahydro-4H-chromene derivatives. 2-Amino-3-cyano-6-methyl-4-phenyl-4H-pyran-5-ethylcarboxylate derivatives can also be prepared in good yield under the same experimental conditions by use of ethyl acetoacetate, aldehydes, and malononitrile. The catalyst, silica-bonded S-sulfonic acid, was reused and recycled without any loss of activity or product yield.

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Acknowledgments

The authors are grateful to the Management of C. Abdul Hakeem College, Melvisharam-632509 (TN), India, for support. The authors also grateful to Dr W. Abdul Hameed, Principal, and Dr M. S. Dastageer, Head of the Research Department of Chemistry, for the facilities and support of the DST-FIST (Government of India)-sponsored Department.

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Authors and Affiliations

  1. Bioactive Organic Molecule Synthetic Unit, Research Department of Chemistry, C. Abdul Hakeem College, Melvisharam, 632 509, Tamil Nadu, India

    K. Aswin, S. Sheik Mansoor, K. Logaiya, S. P. N. Sudhan, V. Saleem Malik & H. Ramadoss

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  1. K. Aswin
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  2. S. Sheik Mansoor
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  3. K. Logaiya
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  4. S. P. N. Sudhan
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  5. V. Saleem Malik
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  6. H. Ramadoss
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Correspondence to S. Sheik Mansoor.

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Aswin, K., Sheik Mansoor, S., Logaiya, K. et al. Reusable silica-bonded S-sulfonic acid catalyst for three-component synthesis of 2-amino-5-oxo-5,6,7,8-tetrahydro-4H-chromenes and 2-amino-4H-pyrans in aqueous ethanol. Res Chem Intermed 40, 2583–2598 (2014). https://doi.org/10.1007/s11164-013-1111-6

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  • DOI: https://doi.org/10.1007/s11164-013-1111-6

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