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Ultrasound-assisted regioselective ring opening of epoxides with nitrogen heterocycles using pyrrolidonium and imidazolium-based acidic ionic liquids

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Abstract

Imidazolium and N-methyl-2-pyrrolidonium ionic liquids under ultrasound irradiation were developed as a green and expeditious approach for C--alkylation and N-alkylation of the nitrogen heterocycles including indoles and imidazoles with aliphatic and aromatic epoxides. Ionic liquids were used with a dual role of catalyst and solvent. The highest yield (85 %) was obtained with N-methyl-2-pyrrolidonium dihydrogen phosphate [H-NMP]H2PO4 as a pyrrolidonium ionic liquid under ultrasound at 50 kHz, with a reaction time of 60 min and reaction temperature of 60 °C. The combination of ionic liquids and ultrasonic irradiation was found to be an effective, green and eco-friendly method for alkylation of indoles and imidazoles.

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Acknowledgments

The authors wish to acknowledge the financial support from Research University (RU) fund (vot. # 05H16) for Universiti Teknologi Malaysia from the Malaysian Ministry of Higher Education (MOHE).

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Authors and Affiliations

  1. Malaysia-Japan International Institute of Technology, International Campus, Universiti Teknologi Malaysia, 54100, Kuala Lumpur, Malaysia

    Masoumeh Zakeri & Mohamed Mahmoud Nasef

  2. Advanced Materials Research Group, Center of Hydrogen Economy, Institute of Future Energy, International Campus, Universiti Teknologi Malaysia, Jalan Semarak, 54100, Kuala Lumpur, Malaysia

    Mohamed Mahmoud Nasef & Ebrahim Abouzari-Lotf

  3. Department of Chemistry, School of Sciences, Alzahra University, Vanak, Tehran, Iran

    Hoda Haghi

Authors
  1. Masoumeh Zakeri
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  2. Mohamed Mahmoud Nasef
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  3. Ebrahim Abouzari-Lotf
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  4. Hoda Haghi
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Corresponding authors

Correspondence to Masoumeh Zakeri or Mohamed Mahmoud Nasef.

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Zakeri, M., Nasef, M.M., Abouzari-Lotf, E. et al. Ultrasound-assisted regioselective ring opening of epoxides with nitrogen heterocycles using pyrrolidonium and imidazolium-based acidic ionic liquids. Res Chem Intermed 41, 10097–10108 (2015). https://doi.org/10.1007/s11164-015-2015-4

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  • DOI: https://doi.org/10.1007/s11164-015-2015-4

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