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KI-Oxone catalyzed ultrasound-promoted synthesis of imidazo[1,2-a]-pyridine-3-carboxylates (IPCs) and evaluation of their anti-tubercular activity

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Abstract

The present work involved ultrasound-promoted KI-Oxone mediated oxidative C–N bond formation from a reaction of β-ketoester and 2-aminopyridines leading to novel functional imidazo[1,2-a]pridine-3-carboxylates (IPCs). The α-halogenation of β-ketoester has been easily carried out by in situ formed I+ OH− species from the KI-Oxone system. IR, NMR, and Mass spectra characterized all derivatives. The structure of the synthesized IPCs was confirmed by X-ray crystallographic analysis. A transition metal-free protocol, one-pot synthesis, non-toxic reagents, benign reaction conditions, high yield, short reaction time, and the synthesis of highly functional IPCs are the remarkable features of the present method. The synthesized IPCs show unusual anti-tubercular activity.

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Acknowledgements

We gratefully acknowledge the financial support from Shivaji University, Kolhapur, Maharashtra (India), under the Research Initiation Scheme [SU/C&U.D.Section/Prop. No.:4/1335].

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Authors and Affiliations

  1. Smt. Kasturbai Walchand College, Sangli, Maharashtra, India

    Vikram Desai, Sandip Nipane & Vijay Sawant

  2. Department of Chemistry, Shivaji University, Kolhapur, Maharashtra, India

    Madhukar Deshmukh

  3. PG Department of Chemistry, P.D.V.P. College, Tasgaon, Sangli, Maharashtra, India

    Vikram Desai & Sandip Patil

  4. Rajarambapu Institute of Technology, Rajaramnagar, Maharashtra, India

    Rajanikant Kurane

  5. Department of Chemistry, Raje Ramrao Mahavidyalaya, Jath, Sangli, Maharashtra, India

    Suresh Patil

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  1. Vikram Desai
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Desai, V., Patil, S., Nipane, S. et al. KI-Oxone catalyzed ultrasound-promoted synthesis of imidazo[1,2-a]-pyridine-3-carboxylates (IPCs) and evaluation of their anti-tubercular activity. J IRAN CHEM SOC 20, 1917–1925 (2023). https://doi.org/10.1007/s13738-023-02808-8

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