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Micellar effects on kinetics and mechanism of Vilsmeier–Haack formylation and acetylation with Pyridines

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Abstract

An efficient preparation of Vilsmeier–Haack formylated and acetylated derivatives with pyridine and substituted pyridines has been developed by employing micelles as catalyst. Their kinetic study reveals a phenomenal rate enhancement in anionic SDS, cationic CTAB, and nonionic TX-100 micellar media. The Vilsmeier–Haack reaction follows second order kinetics. Piszkiewicz’s co-operativity model was used to interpret the results in micellar media. The observed activation parameters ΔH and ΔS values were calculated from Eyring’s plots. The main features of this study were easy process, mild reaction conditions and readily available reagents.

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Acknowledgements

The author is grateful to Professor K.C. Rajanna, (Osmania University, Hyderabad) for his consistent guidance and inspiring discussions during the work. The author thanks Nawab Shah Alam Khan Center for Post Graduate Studies and Research, Hyderabad, India, for providing necessary research facilities to the Chemistry Department.

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Authors and Affiliations

  1. Department of General Science, Ibn Sina National College for Medical Studies, Jeddah, Kingdom of Saudi Arabia

    Tasneem Mohammed, Aejaz Abdullatif Khan & S. M. Shakeel Iqubal

  2. Department of Pharmaceutical Chemistry, College of Pharmacy, Najran University, Najran, Kingdom of Saudi Arabia

    Bandar A. Alyami

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  1. Tasneem Mohammed
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  2. Aejaz Abdullatif Khan
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  3. S. M. Shakeel Iqubal
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  4. Bandar A. Alyami
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Correspondence to S. M. Shakeel Iqubal.

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Mohammed, T., Khan, A.A., Iqubal, S.M.S. et al. Micellar effects on kinetics and mechanism of Vilsmeier–Haack formylation and acetylation with Pyridines. Chem. Pap. 76, 2615–2621 (2022). https://doi.org/10.1007/s11696-022-02066-7

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