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A simple protocol for the michael addition of indoles with electron deficient olefins catalysed by TBAHS in aqueous media and their broad spectrum antibacterial activity

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Abstract

Tetrabutylammonium hydrogen sulfate catalysed addition of indoles to electron deficient olefins in water generated the corresponding Michael adducts in good to excellent yield. The Michael addition of indole occurred regioselectively at position 3 and the N-alkylated products have not been observed. The synthesized compounds were tested for their antibacterial activity against four microorganisms namely, E. coli NCIM 2931, S. aureus NCIM 5021, P. vulgaris NCIM 2813, P. aeruginosa NCIM 5029 by micro dilution method. These compounds showed MIC (Minimum Inhibitory Concentration) values in the range of 0·16–2·67 µM.

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Authors and Affiliations

  1. Organic Chemistry Division, Central Leather Research Institute, Adyar, Chennai, 600 020, India

    M. Damodiran, R. Senthil Kumar & Paramasivan T. Perumal

  2. Department of Biotechnology, Indian institute of Technology Madras, Adyar, Chennai, 600 036, India

    P. M. Sivakumar & Mukesh Doble

Authors
  1. M. Damodiran
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  2. R. Senthil Kumar
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  3. P. M. Sivakumar
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  4. Mukesh Doble
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  5. Paramasivan T. Perumal
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Correspondence to Paramasivan T. Perumal.

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Damodiran, M., Kumar, R.S., Sivakumar, P.M. et al. A simple protocol for the michael addition of indoles with electron deficient olefins catalysed by TBAHS in aqueous media and their broad spectrum antibacterial activity. J Chem Sci 121, 65–73 (2009). https://doi.org/10.1007/s12039-009-0007-x

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  • DOI: https://doi.org/10.1007/s12039-009-0007-x

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