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Sodium carbonate-catalyzed Claisen–Schmidt condensation: one-pot synthesis of highly functionalized cyclohexenones under environmental conditions

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Abstract

In this investigation, a practical green chemistry procedure for synthesis of highly functionalized cyclohexenone derivatives according to the Claisen–Schmidt condensation and Michael reaction using acetoacetanilide, acetophenone, and appropriate aromatic aldehydes in the presence of 15 mol% of Na2CO3 as a catalyst in H2O/EtOH at ambient conditions is described. This methodology is of interest due to the use of water/ethanol as a solvent without the use of any harmful and toxic organic solvents and toxic metals as catalysts. Neutral conditions, excellent yields, a short reaction time, a simple work-up procedure of products and use of an inexpensive catalyst are some of the main advantages of this environmentally benign process. Also, there is no need for column chromatography to obtain pure products.

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Acknowledgments

The University of Sistan and Baluchestan is thanked for supporting this work.

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Authors and Affiliations

  1. Department of Chemistry, Faculty of Science, University of Sistan and Baluchestan, P.O. Box 98135-674, Zahedan, Iran

    Mir Rasul Mousavi & Malek Taher Maghsoodlou

  2. Faculty of Science, Payame Nour University of Khoy, Khoy, Iran

    Mir Rasul Mousavi

  3. Sina 24 hour Clinic, Marand, Iran

    Hadigheh Gharari

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  1. Mir Rasul Mousavi
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  2. Malek Taher Maghsoodlou
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  3. Hadigheh Gharari
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Correspondence to Mir Rasul Mousavi.

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Mousavi, M.R., Maghsoodlou, M.T. & Gharari, H. Sodium carbonate-catalyzed Claisen–Schmidt condensation: one-pot synthesis of highly functionalized cyclohexenones under environmental conditions. Res Chem Intermed 42, 2233–2246 (2016). https://doi.org/10.1007/s11164-015-2146-7

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