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Novel α-sulfamidophosphonate analogues of fotemustine: efficient synthesis using ultrasound under solvent-free conditions

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Abstract

The development of new clean and effective processes for the preparation of new elaborated compounds is currently an important research axis in organic chemistry, thus in recent years, the application of ultrasound has gained a very important development in synthetic organic chemistry. In this context, we have developed a new access route to sulfamidophosphonate analogues of fotemustine which is known to be a cytotoxic alkylating agent, using ultrasonic irradiation as a source of activation of this type of reaction, starting from sulfonamide, triethylphosphite, and various aldehydes via three component reaction. A wide range of substrates is compatible in this reaction, producing good yields (70–85%) in short time (30–60 min). All products were carefully characterized by 1H, 13C NMR as well as IR and HRMS.

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Acknowledgements

This work was supported financially by The General Directorate for Scientific Research and Technological Development (DG-RSDT), Algerian Ministry of Scientific Research, Applied Organic Chemistry Laboratory (FNR 2000).

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Authors and Affiliations

  1. Laboratory of Applied Organic Chemistry, Synthesis of Biomolecules and Molecular Modelling Group, Sciences Faculty, Chemistry Department, Badji-Mokhtar - Annaba University, Box 12, 23000, Annaba, Algeria

    Meriem Guerfi, Malika Berredjem, Abdeslem Bouzina & Khadidja Otmane Rachedi

  2. Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Umm Al-Qura University, Makkah Almukkarramah, Saudi Arabia

    Taibi Ben Hadda

  3. Faculté de Pharmacie-ISPB, EA 4446 Bioactive Molecules and Medicinal Chemistry, SFR Santé Lyon-Est CNRS UMS3453-INSERM US7, Université Lyon 1, CEDEX 8, 69373, Lyon, France

    Christelle Marminon

Authors
  1. Meriem Guerfi
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  2. Malika Berredjem
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  3. Abdeslem Bouzina
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  4. Taibi Ben Hadda
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  5. Christelle Marminon
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  6. Khadidja Otmane Rachedi
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Correspondence to Malika Berredjem.

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Guerfi, M., Berredjem, M., Bouzina, A. et al. Novel α-sulfamidophosphonate analogues of fotemustine: efficient synthesis using ultrasound under solvent-free conditions. Monatsh Chem 151, 1859–1865 (2020). https://doi.org/10.1007/s00706-020-02711-5

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  • DOI: https://doi.org/10.1007/s00706-020-02711-5

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