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Ammonium acetate as a catalyst and/or reactant in the reaction of dimedone, aromatic aldehyde, and malononitrile: synthesis of tetrahydrobenzo[b]pyrans and hexahydroquinolines

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Abstract

The reaction of aromatic aldehydes, dimedone, and malononitrile in the presence of ammonium acetate has afforded tetrahydrobenzo[b]pyrans instead of polyhydroquinolines under both grinding and reflux conditions; thus ammonium acetate acts as a catalyst for this transformation instead of a reactant. Polyhydroquinoline derivatives were also synthesized via a one-pot condensation of aromatic aldehydes, malononitrile and an enaminone, which was prepared by the reaction of dimedone and ammonium acetate, in refluxing ethanol in high yields.

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Acknowledgments

The authors sincerely acknowledge the Research Office of Azarbaijan Shahid Madani University for financial support.

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Authors and Affiliations

  1. Chemistry Department, Faculty of Science, Azarbaijan Shahid Madani University, Tabriz, Iran

    Adeleh Moshtaghi Zonouz, Somaieh Okhravi & Davood Moghani

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  1. Adeleh Moshtaghi Zonouz
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  2. Somaieh Okhravi
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  3. Davood Moghani
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Correspondence to Adeleh Moshtaghi Zonouz.

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Moshtaghi Zonouz, A., Okhravi, S. & Moghani, D. Ammonium acetate as a catalyst and/or reactant in the reaction of dimedone, aromatic aldehyde, and malononitrile: synthesis of tetrahydrobenzo[b]pyrans and hexahydroquinolines. Monatsh Chem 147, 1819–1824 (2016). https://doi.org/10.1007/s00706-016-1683-0

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  • DOI: https://doi.org/10.1007/s00706-016-1683-0

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