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Iodine-mediated efficient synthesis of pyrano[2,3-c]pyrazoles and their antimicrobial activity

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Abstract

s-cis-(E)-1-(5-Hydroxy-3-methyl-1-phenyl-1H-pyrazol-4-yl)-3-arylprop-2-en-1-ones (pyrazolyl chalcones), prepared from 1-phenyl-3-methyl-4-acetylpyrazol-5-one and aromatic aldehydes, were oxidatively cyclized to pyrano[2,3-c]pyrazoles using iodine in excellent yield (90–98 %). The structure of pyrano[2,3-c]pyrazoles was established using NMR, 2D NMR, and HRMS techniques. Among the synthesized pyrano[2,3-c]pyrazoles, 6-(4-chlorophenyl)-3-methyl-1-phenylpyrano[2,3-c]pyrazol-4(1H)-one and 6-[3-(4-methoxyphenyl)-1-phenyl-1H-pyrazol-4-yl]-3-methyl-1-phenylpyrano[2,3-c]pyrazol-4(1H)-one displayed significant antimicrobial activity against Staphylcococcus aureus having MIC 0.46 × 10−2 and 0.32 × 10−2 µM, respectively.

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Acknowledgments

We thank University Grants Commission, New Delhi, for financial support and award of teacher fellowship to Mahavir Parshad under FIP scheme 12th plan period.

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Authors and Affiliations

  1. Department of Chemistry, Guru Jambheshwar University of Science and Technology, Hisar, Haryana, India

    Mahavir Parshad, Vikas Verma & Devinder Kumar

Authors
  1. Mahavir Parshad
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  2. Vikas Verma
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  3. Devinder Kumar
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Corresponding author

Correspondence to Devinder Kumar.

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Parshad, M., Verma, V. & Kumar, D. Iodine-mediated efficient synthesis of pyrano[2,3-c]pyrazoles and their antimicrobial activity. Monatsh Chem 145, 1857–1865 (2014). https://doi.org/10.1007/s00706-014-1250-5

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