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Iodine mediated a simple strategy for the synthesis of β,γ-unsaturated-α-ketoesters and its application for the synthesis of 4,5-dihydropyrazole derivatives

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Abstract

Novel and efficient method for the synthesis of a series of β,γ-unsaturated-α-ketoesters under mild conditions was developed. This one-step protocol was achieved by the reaction of electron-rich aromatic aldehydes and pyruvates in the presence of 10 mol% of molecular iodine in solvent-free condition at 80 °C temperature. A wide variety of substrates bearing electron releasing groups on aromatic ring were well tolerated and delivered corresponding β,γ-unsaturated-α-ketoesters in moderate to good yields. These β,γ-unsaturated-α-ketoesters have been further utilized in the synthesis of 4,5-dihydropyrazole derivatives.

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Acknowledgements

The authors gratefully acknowledge the financial support received from the Department of Science and Technology (DST), New Delhi (File No: YSS/2015/001581). The authors also gratefully acknowledge the SAIF, NIT, Warangal, for providing all the spectroscopic and analytical data.

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Authors and Affiliations

  1. Department of Chemistry, Palamuru University, Mahabubnagar, Telangana, 509001, India

    Asha Begum Shaik & Vijaya Laxmi Somarapu

  2. Department of Chemistry, Koneru Lakshmaiah Education Foundation, Guntur, Andhra Pradesh, 522502, India

    Anil Pommidi & Anindita Chatterjee

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  1. Anil Pommidi
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  2. Asha Begum Shaik
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  3. Anindita Chatterjee
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  4. Vijaya Laxmi Somarapu
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Correspondence to Vijaya Laxmi Somarapu.

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Pommidi, A., Shaik, A.B., Chatterjee, A. et al. Iodine mediated a simple strategy for the synthesis of β,γ-unsaturated-α-ketoesters and its application for the synthesis of 4,5-dihydropyrazole derivatives. J IRAN CHEM SOC 17, 1545–1553 (2020). https://doi.org/10.1007/s13738-020-01872-8

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  • DOI: https://doi.org/10.1007/s13738-020-01872-8

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